List of Monk characters

This is a list of characters in the comedy-drama TV series Monk.

Main characters

Name	Portrayed by	Occupation/Status
Adrian Monk	Tony Shalhoub	SFPD police detective (reinstated)
Natalie Jane Davenport Teeger	Traylor Howard	Assistant to Adrian Monk
Captain Leland Stottlemeyer	Ted Levine	SFPD Police captain: Robbery Homicide
Lieutenant Randall "Randy" Disher	Jason Gray-Stanford	SFPD Police lieutenant: Robbery Homicide
Sharona Fleming	Bitty Schram	Nurse and Monk's former assistant

Secondary characters

Julie Teeger

Julie Teeger
First appearance	"Mr. Monk and the Red Herring"
Portrayed by	Emmy Clarke (2005-present)
In-universe information
Gender	Female
Family	Natalie Teeger (mother) Mitch Teeger (father; deceased)

Julie Teeger, played by Emmy Clarke, is the daughter of Adrian Monk's assistant, Natalie. Julie was introduced to the show during the third season (episode 10, "Mr. Monk and the Red Herring") where she bonded with Monk after he rescued her pet fish. In that episode she is 11 years old. Since then, Julie has appeared in several episodes of the show, usually in minor roles. In "Mr. Monk Goes to a Fashion Show," Julian Hodge (Malcolm McDowell) invites Julie to participate in a fashion show.

In "Mr. Monk and the Big Game", Julie and her friends on the high school basketball team hire Monk to investigate when their coach is found dead in the locker room following a practice. They (correctly) suspect that this was no accident. Natalie temporarily coaches the team, with Monk as her assistant.

Natalie and Julie fill the gap left when Sharona left Monk and went with her son, Benjy, to remarry her ex-husband. She plays a critical role in the Monk episode "Mr. Monk and the Birds and the Bees," in which Monk has to give her "the talk" when she starts dating an older guy. A T-shirt with a picture of her previous boyfriend is the clue to a double murder, making her have an even more integral role. In the season 6 episode, "Mr. Monk and the Three Julies," it is revealed that Julie has received her driver's license. Also, it is revealed that after the murder of the other two Julie Teegers in San Francisco, she is the only Julie Teeger for 1,000 miles. In "Mr. Monk is Underwater," it is stated that her age is seventeen. She is later shown to be trying to be an actress, with her performance being the key to solving a murder. In "Mr. Monk and The End, Part One" it is revealed that she is going to the University of California at Berkeley to study Theatre Arts, and that even though she will only be a half-hour away from San Francisco, she will not stay living at home.

Charles Kroger

Dr. Charles Kroger
First appearance	"Mr. Monk and the Candidate"
Last appearance	"Mr. Monk Paints His Masterpiece"
Portrayed by	Stanley Kamel (2002-2008)
In-universe information
Occupation	Psychiatrist
Spouse	Madeline Kroger
Children	Troy Kroger

Dr. Charles Kroger (played by Stanley Kamel) was Monk's beloved psychiatrist. Stanley Kamel died at the age of 65 in 2008 after suffering a heart attack, and as Monk was on hiatus as of April 2008 (Due to the WGA Strike). In May 2008, it was announced on the official Monk website that Hector Elizondo would portray Adrian's new psychiatrist, Dr. Neven Bell.

Perhaps the most tolerant of all of Adrian Monk's friends, Kroger is a psychiatrist who serves as the closest thing to a rock for Monk. While he does engage in talk therapy, he does not prescribe an SSRI medication, which is commonly used by psychiatrists to treat OCD, because Adrian doesn't like to take drugs and when he did, in the episode "Mr. Monk Takes His Medicine", although Monk lost many of his phobias, he also lost his ability to solve crimes. Kroger is instrumental in trying to get Monk reinstated as a detective, while discussing his problems and progress as a person. Most of Kroger's scenes help move Monk's character forward. Similarly, Dr. Kroger has also (usually unintentionally) helped Monk solve several cases. In "Mr. Monk Gets a New Shrink" he temporarily quit after his maid was murdered, since the police thought that one of his patients was responsible.

Kroger is also the subject of an ongoing feud between Monk and Harold Krenshaw, another patient with similar problems. While very forgiving, even Kroger gets fed up with Monk from time to time, most heavily demonstrated in one episode ("Mr. Monk and the Sleeping Suspect") where Kroger came back from vacation and saw Monk standing outside his home. Kroger simply instructed the cab driver to just keep driving and kept his head low to avoid Monk. On another occasion in "Mr. Monk and the Garbage Strike", when the city stopped collecting garbage, Monk sent his garbage to Dr. Kroger's house. When questioned about it, Monk denied it before Kroger told him it was specifically sorted, boxed, and written in his handwriting.

On the other hand, there have also been several cases in which Dr. Kroger has been the only person capable of getting through to Monk during difficult situations, such as when Monk was brainwashed by a duplicitous cult leader played by Howie Mandel ("Mr. Monk Joins a Cult").

It was revealed in the 15th episode of Season 3 ("Mr. Monk and the Election"), that Kroger is married and has children (a son), and is also Jewish. In the first episode of Season 5 ("Mr. Monk and the Actor"), Monk wants to take up the entire week with therapy sessions. Kroger says he does not like working on the weekends so he can spend time with his wife and kids. In the episode "Mr. Monk Gets a New Shrink", it is revealed that he has a wife, Madeline, and a rebellious adolescent son, Troy, who denies that he is their child.

Kroger has a stormy relationship with his son, and was forced to take a paternity test three times at the "request" of his son. Troy calls his parents by their first names and knows Lt. Randy Disher from possibly being arrested. Disher asked if Troy had kept out of trouble, to which Troy said "no". Troy later appears in the Season 6 episode "Mr. Monk and the Buried Treasure". In this episode, while skateboarding with two friends, he finds a map leading to what he assumes is money. He and his friends ask Monk to help them, saying it is a school project. Monk agrees to help them, and they eventually find it. Monk, however, later discovers he's been tricked and tells Troy to come with him back to where the buried treasure was, leading to them temporarily being trapped in Troy's car. By the end of the episode Troy has a better relationship with his father.

Prior to the beginning of season 7 Stanley Kamel died suddenly of a heart attack, and the same explanation was used to explain Dr. Kroger's departure from the series. Monk is understandably quite disturbed by the event, but manages to recover with the aid of his new psychiatrist, Dr. Neven Bell.

Neven Bell

Neven Bell
First appearance	"Mr. Monk Buys a House"
Portrayed by	Hector Elizondo
In-universe information
Gender	Male
Occupation	Therapist

Dr. Neven Bell (Hector Elizondo) is Adrian's new therapist beginning in the Season Seven premiere (Mr. Monk Buys a House) after Adrian's original therapist, Dr. Kroger, died of a heart attack. This character was introduced after Stanley Kamel, who played Dr. Kroger, died of a heart attack between production of Seasons Six and Seven.

Though Adrian is skeptical of his new therapist at first, Dr. Bell was able to win his confidence though several small gestures (he begins the appointment at the exact second it was scheduled and has Adrian's favorite bottled water available, a supply of wipes handy during their introductory handshake, and a painting in his office which previously belonged to the late Dr. Kroger.)

Additionally, Natalie pointed out that Dr. Bell's name (Neven) is a palindrome as a comfort to Adrian. Adrian, however, points out that it isn't a "perfect" palindrome, because of the first "N" being capitalized.

Dale "The Whale" Biederbeck

Dale Biederbeck
First appearance	"Mr. Monk Meets Dale the Whale"
Portrayed by	Adam Arkin (2002) Tim Curry (2004) Ray Porter (2008)
In-universe information
Alias	Dale "The Whale" Biederbeck

Dale "The Whale" Biederbeck is a recurring villain, appearing in 3 episodes so far. In season 1, he is played by Adam Arkin, in season 2 by Tim Curry, and in season 6 by Ray Porter, all of them wearing fat suits. A very rich and well-connected financier, Biederbeck is arrogant, brilliant, and ruthless. Adrian Monk claims that Biederbeck owns "half the city" (of San Francisco), and has an option on the other half. He gets his nickname from his morbid obesity (caused by overeating, supposedly attributed to the death of his mother). In his first and second appearances, he weighs upwards of 800 pounds (360 kilograms), and is unable to leave his bed. By the time of his third appearance, "Mr. Monk Is On The Run, Part II" he has lost enough weight to get around in a wheelchair.

In his first appearance, "Mr. Monk Meets Dale the Whale" Biederbeck is the primary suspect in the slaying of a judge who issued a costly antitrust ruling against him. Several clues point to his being the killer, but it seems impossible because he is incapable of leaving his bedroom. It is also revealed in this episode that Monk harbors a severe hatred of Biederbeck, who sued his late wife Trudy and her newspaper after she wrote an unflattering article about him (calling him the "Genghis Khan of world finance"). Unlike many rich men, Biederbeck goes to extreme lengths to avoid publicity. He sued Trudy and the paper that published the article in a drawn-out libel suit that he knew he couldn't win, just to torment her. The legal costs forced the Monks to sell their first home, which Biederbeck snapped up and which he now claims to use to store his collection of pornography. Because Trudy was killed a short time later, Monk feels that Biederbeck stole one of the last years of her life. However, at the end of the episode, Monk proves that Biederbeck and his personal doctor conspired to kill the judge, and the doctor promptly turns state's evidence on Dale.

Biederbeck reappears in Season Two's "Mr. Monk Goes to Jail." Although he's been convicted of murder, he is adjusting to life in prison quite easily. He has an inmate to act as his personal servant, luxurious furniture, a TV, and just about everything one would not normally find in a prison environment — except a window. After a condemned prisoner is poisoned less than an hour before his execution, suspicion falls on Biederbeck, to whom the dead man owed $1,200. Both he and Monk know that Biederbeck wouldn't kill anyone over such a petty sum (as he says with a laugh, "I wouldn't bend down to pick up $1,200, even if I could"), but until the killer is caught, the prison is refusing to install Biederbeck's window. He offers Monk a deal: find the killer, and Biederbeck will share what he knows about Trudy's murder.

Even though Sharona tells him not to, Monk takes the case on the off-chance that Biederbeck is telling the truth. After Monk solves the case, Dale reveals that Trudy was, contrary to Monk's belief, indeed the intended victim of the car bomb. He also states that Monk should look for a man named Warrick Tennyson who can be found in Manhattan, New York. This gives Monk his first real lead on Trudy's death. The episode ends on an ominous note, as Biederbeck watches Monk's plane depart for New York through his newly installed window and smiles, "Bon voyage, Mr. Monk."

In the Season 3 premiere, Monk finds Tennyson, who confesses to being hired to kill Trudy, and identifies the man who hired him as having a six-fingered hand. To Sharona's, and even Monk's surprise, it's evident that Biederbeck was telling the truth after all.

The reason becomes clear in the two-part episode "Mr. Monk Is On The Run," when Monk is framed for murder of the six-fingered man who hired Tennyson. Dale is revealed to be the mastermind of the plot, and of a simultaneous plot to murder the Governor of California. The Lieutenant Governor, who is on Dale's payroll, would then pardon Dale, completing Dale's revenge by setting him free and putting Monk in jail. But Monk foils Dale's plan, and a corrupt sheriff who had been responsible for framing Monk turns state's evidence. As a result, all of Dale's privileges are revoked at the prison: His custom bed, telephone, and laptop are confiscated; special meal deliveries, manicure appointments, and his window is removed; and he is reduced to sleeping in a cramped bunk bed, with only a wheelchair to move around in and eating prison food in the cafeteria with the other inmates.

Biederbeck also makes a brief appearance in the novel "Mr. Monk Goes to Germany," by Lee Goldberg. Monk telephones Biederbeck from Germany when he suspects that one of Dr. Kroger's colleagues, a psychiatrist with a six-fingered hand, is the man who killed Trudy. Since the doctor was giving a lecture at Berkeley in the same week Trudy was killed, thanks to a grant from one of Biederbeck's foundations, Monk suspects Biederbeck of being the killer. Biederbeck smugly refuses to confirm or deny Monk's suspicions, but later Monk proves that the doctor is not Trudy's killer (the novel was written before, but published after, the airing of "Mr. Monk Is On The Run," and Goldberg's foreword acknowledged the discontinuity).

Benjy Fleming

Benjamin Fleming
First appearance	"Mr. Monk and the Candidate"
Last appearance	"Mr. Monk and the Employee of the Month" (episode) "Mr. Monk and the Two Assistants" (book)
Portrayed by	Max Morrow (2002) Kane Ritchotte (2002-2004)
In-universe information
Family	Sharona Fleming (mother) Trevor Howe (father) Douglas Fleming (maternal grandfather; deceased) Cheryl Fleming (maternal grandmother) Gail Fleming (maternal aunt)

Benjamin "Benjy" Fleming is the son of Sharona Fleming. He was played by Kane Ritchotte in the pilot and second season and by Max Morrow in the rest of the first season, excluding the pilot. This is because Ritchotte lives on the west coast, where the pilot was filmed (in Vancouver) and where the second season was filmed (in Los Angeles), while Morrow lives on the east coast, where the remainder of the first season was filmed (in Toronto).

Monk bonds with Benjy but has his problems in relating since he never did the things normally associated with kids growing up. As a result he is clueless in giving Benjy a pep talk about baseball ("Mr. Monk Goes to the Ballgame") since Benjy has to show him how to hold a bat. In "Mr. Monk and the Playboy" when Sharona tells him of her less than reputable past which was about to be revealed if Mr. Monk persisted in his investigation even though she knew Benjy would be open to ridicule and perhaps even lose respect for her, Benjy reassures her that he could handle it.

He is in little league ("Mr. Monk Goes to the Carnival"). He is a sixth-grader and wants to be a writer ("Mr. Monk Takes a Vacation").

He eventually returned to New Jersey with his mother to reunite with his father, Trevor Howe.

His first appearance in any Monk-related story since he and Sharona left the television show was in the Lee Goldberg novel Mr. Monk and the Two Assistants, where Sharona returns to San Francisco because her husband was accused of murder. Benjy and his mother were mentioned in "Mr. Monk Is On The Run, Part 2," having sent flowers for the presumed deceased Monk and flying in to attend his funeral.

Trudy Monk

Trudy Monk
First appearance	"Mr. Monk and the Candidate" (mention)
Portrayed by	Stellina Rusich (2002-2003) Lindy Newton (2006) Melora Hardin (2004-present)
In-universe information
Gender	Female
Occupation	Journalist
Family	Dwight Ellison (father) Marcia Ellison (mother) Jack Monk, Sr. (father-in-law) Ambrose Monk (brother-in-law) Jack Monk, Jr. (half-brother-in-law)
Spouse	Adrian Monk (married at time of death)

Trudy Anne Monk (née Ellison) (Melora Hardin) is Monk's deceased wife. Her husband's attempt to solve her murder is the show's longest-running plot arc. She has formerly been played by Stellina Rusich during the first and second seasons, and Hannah Contrucci as young Trudy during the fourth season. Lindy Newton plays Trudy in a college flashback in the fifth season.

Trudy Monk was born in Los Angeles in 1962. She attended the Ashton Preparatory School and graduated valedictorian in 1977 at the age of 15. She did not date very much while there, expecting to know who the right man would be once she found him. She graduated from the University of California, Berkeley. She met her future husband Adrian while he was working there at the library. Adrian and Trudy married on August 8, 1990.

In 1993, Trudy was involved in a lawsuit with financier Dale Biederbeck (a.k.a. Dale the Whale) because she referred to him as the "Genghis Khan of Finance". The Whale was unable to win the lawsuit, but the Monks were forced to sell their house paying for their lawyer. Adrian harbors an intense hatred for the Whale because of the pain he caused Trudy, saying that he stole a year of her life. The Whale remains an important adversary of Adrian's, especially when it is revealed that he had a role in Trudy's death. Adrian later proves the Whale guilty of murder and sees him jailed.

In Adrian's words, Trudy "enjoyed poetry, was often barefoot, and kept every promise she ever made". In "Mr. Monk Takes Manhattan", Adrian offers a glimpse into her mindset by turning Warrick Tennyson's morphine back on after he had turned it off claiming Trudy would have wanted him to.

Trudy Monk was murdered on a snowy December 14, 1997 with a bomb containing 3 lbs of plastic explosives powered by 10 20V magnesium batteries that detonated under the front seat while she was on an errand to get cough medicine for Adrian's brother Ambrose. Ambrose blames himself for Trudy's death, and his guilt led to a 7-year rift between the brothers.

In "Mr. Monk Can't See a Thing", Adrian reveals that Trudy lived for 20 minutes after the bomb went off. Her last words to a paramedic were "bread and butter", a message to Adrian meaning that she would never leave him, as this was something she always told her husband when they had to temporarily let go of each other for some reason or another.

The bomb was built by Warrick Tennyson. Tennyson was hired by a six-fingered man whom he could not identify. Since the homicide's occurrence, Adrian had believed all along that he was the intended target, with Trudy being an innocent victim. The intense guilt contributed to and intensified his nervous breakdown, his obsessive-compulsive manifestations, and his bizarre phobias. In "Mr. Monk Goes to Jail", Dale the Whale reveals that the car bomb was actually intended for her, not him. Discovering that Trudy was the true target, Adrian is seen to be visibly affected by this piece of news. In "Mr. Monk Bumps His Head", Adrian attempts to find this 6-fingered man by purchasing a picture of him. The picture turns out to be a fake. In "Mr. Monk and Mrs. Monk", Natalie overhears a woman who looks like Trudy say that she faked her own death to protect Adrian. Adrian begins to believe this might be true, but in the end, it turns out that this woman has attempted to pass herself off as the real Trudy in order to get the key to Trudy's old storage unit. In "Mr. Monk Is Up All Night", Adrian sees a Brazilian woman whom he chases for several blocks for no apparent reason. At the end of the episode, it is revealed that the reason he was drawn to her is that she received a cornea transplant from an organ donor, who turned out to be Trudy.

During the sixth season's finale, "Mr. Monk Is On The Run", Adrian finds the six-fingered man, named Frank Nunn, but unfortunately he is shot and killed by a corrupt cop hired by Dale the Whale in a plot to incriminate Adrian. By the end of the episode, Adrian confronts Dale, telling him that the police searched Nunn's home and discovered from some old letters that Nunn was hired by a man named "The Judge". Adrian believes Dale knows the identity of "The Judge", but so far, Dale has not revealed any further information.

In "Mr. Monk and the End Part 1", the audience learns that "The Judge" (played by Craig T. Nelson) is an actual judge the gang knows, and just visited to obtain a search warrant. The Judge admits in a phone conversation that he killed Trudy. Monk also discovers that Trudy had left a videotape to him containing a video she wanted him to watch in case harm befell her.

Ambrose Monk

Ambrose Monk
First appearance	"Mr. Monk and the Three Pies"
Portrayed by	John Turturro (2004, 2005, 2008)
In-universe information
Gender	Male
Occupation	Writer of owner's manuals
Family	Jack Monk, Sr. (father) Adrian Monk (brother) Jack Monk, Jr. (half-brother) Trudy Monk (sister-in-law; deceased)

Ambrose Monk, played by John Turturro, is the brother of Adrian Monk. He suffers from agoraphobia. He can be seen in person in three episodes, "Mr. Monk and the Three Pies", "Mr. Monk Goes Home Again" and "Mr. Monk's 100th Case", as well as in home movies as shown in "Mr. Monk Is on the Air". He has a romantic interest in Natalie Teeger, Adrian's assistant. Ambrose writes owner's manuals for many different consumer products in multiple languages which he taught himself. The house he lives in is cluttered with his work, piles of newspapers, and filing cabinets which are stuffed with his father's mail spanning the entirety of his father's absence.

He blames himself for the death of Adrian's wife, Trudy. At Ambrose's request, Trudy was out buying him cough medicine when she was murdered by a bomb planted under the front seat of her car. Guilt-ridden, Ambrose avoided all contact with Adrian for seven years after the incident.

When Adrian and Ambrose were children, they shared a strong bond with their father. This may have been due to his strict rules, such as not ever entering his office, and the boys' social seclusion, causing a sort of dependency. In the episode "Mr. Monk meets his Dad", Jack Monk explains to Adrian in his truck that he opened up a fortune cookie which said 'Stand by your man', so he followed his own path and left. Ever since, Ambrose has been obsessed with the idea of his return, even to the point of preparing a dinner plate for him every night, just in case. Adrian feels differently, believing his father will never return. However, their father showed up at Ambrose's doorstep to leave a note. Adrian and Ambrose, who were in an ambulance at the time due to the fact that they thought he had been poisoned by a Neptune candy bar, missed their father's appearance but the note congratulated Ambrose on finally leaving the house. Ambrose has left the house two other times: when it was on fire, and the second when he was visiting Trudy's grave (in the same episode).

In "Mr. Monk's 100th Case" he appears in a documentary about Adrian, and says his brother held the family together after Jack Monk left them. Both himself and his mother became unable to deal with the outside world, and Adrian Monk saved them (likely by being able to go to school and go shopping for needed items, like groceries). He greatly respects his brother's ability to cope with the outside world.

The relationship between Adrian and Ambrose can be seen as a parallel to the relationship between Sherlock Holmes and his brother Mycroft, in that Ambrose is acknowledged as more intelligent than his brother but does not apply himself to outside work. In the case of the Holmes brothers though, Mycroft's unwillingness to investigate is based on his own sedentary nature rather than agoraphobia.

Jack Monk

Jack Monk
First appearance	"Mr. Monk Meets His Dad"
Portrayed by	Dan Hedaya (2006)
In-universe information
Gender	Male
Occupation	Truck driver
Family	Trudy Monk (daughter-in-law; deceased)
Children	Adrian Monk (son) Ambrose Monk (son) Jack Monk, Jr. (son)

Jack Monk, played by Dan Hedaya, is Monk's father. He appears in the episode entitled "Mr. Monk Meets His Dad". Jack, the father of both Ambrose and Adrian Monk, abandoned his young family while running to pick up an order of Chinese food. Adrian was only eight years old and his father's abandonment is seemingly the catalyst for both Adrian and Ambrose's psychological illnesses. After leaving, Jack isn't heard from for over forty years. During that time he fathered yet another son, 31 year old Jack Jr. whom Jack proudly brags about to his co-workers as a genius doctor (but later admits to Adrian's surprise that Jack Jr. is an unemployed buffoon who smokes marijuana all day and steals money from his wallet). Jack finally makes an appearance - albeit an unnoticed one - at Ambrose's door to leave him a congratulatory note on Ambrose's exit from the house (though this was because he was being driven to the hospital in an ambulance at the time, having eaten what he thought was a poisoned candy bar).

Very little is known about Jack Monk's personal history. It is established by Adrian in the above-mentioned episode that Jack wrote school textbooks as his career of choice (similar to his other son, Ambrose), indicating some level of education. Not much explanation is provided for how he ends up in the state explored in "Mr Monk Meets His Dad."

When Jack finally shows up in person, he is working for a Midland, Texas-based trucking company and had been stopped in San Francisco for running a red light. He was arrested and was placed in jail for shoving the police officer who had stopped him. Initially, Adrian's reception to his father was icy and uninviting, but the two later reconciled over a road trip.

Although the elder Monk is portrayed as eccentric, unpleasant, and erratic, he is also apparently quite intelligent, possibly implying that Ambrose and Adrian inherited at least some of their prodigious mental abilities from their father.

Jack Monk, Jr.

Jack Monk, Jr.
First appearance	"Mr. Monk's Other Brother"
Portrayed by	Steve Zahn (2009-present)
In-universe information
Gender	Male
Family	Jack Monk (father) Adrian Monk (half-brother) Ambrose Monk (half-brother)

Jack Monk Jr. (played by Steve Zahn) is Monk's half-brother. His father (and Monk's father) left him and his mother after 10 years when their family was together. Jack Monk Jr. met Monk after he was arrested and imprisoned for attempting to sell cars that weren't his. He escaped from prison, but was framed for a murder right after. Jack went to his half-brother, Monk, in hopes that Monk could clear his name.

Jack Monk Jr. appears to be a pathological liar, and often swears "hand to God" that he is telling the truth when he really is not. He also has an obsession with the country of Paraguay, suggested to be due to the country's supposed lack of an extradition treaty with the United States.

His name was cleared and he went back to prison, though Randy's handcuff key "went missing".

Recurring Characters and Special Appearances

Maria Disher

Maria Disher is Lt. Disher's mother. In the second season episode "Mr. Monk Gets Married," she marries Dalton Pedrone, who turns out to be a murderer.

Harvey Disher

Harvey Disher is Lt. Disher's late uncle who dies in season 5 episode "Mr. Monk Visits A Farm".

Kevin Dorfman

Kevin Dorfman (Jarrad Paul) was Monk's annoying, talkative upstairs neighbor (according to Monk, "one time, he had a sore throat, he talked for two and a half hours about how much it hurt him to talk", though this appears to be a family trait) until he was killed in "Mr. Monk and the Magician." He was often seen cooking (with Monk). He first appeared in "Mr. Monk and the Paperboy", where he won $43 million in the lottery, although his "girlfriend" tried to hide it from him with the object of eventually getting it all. However he lost it all on bad investments, golddiggers, two wives and sleazy accountants. A CPA, he had two sisters and could recall all eight times he ate egg salad sandwiches. Kevin worked in a coffee shop in Aspen, Colorado and accompanied Monk when his father-in-law asked him to investigate a cheating problem on a game show. According to Kevin, a pencil with chew marks on it is a "collectible". An amateur magician, he is killed the night of his professional debut in the episode "Mr. Monk and the Magician," by strangulation, due to unknowingly discovering a fellow magician's drug trafficking.

Dwight Ellison

Dwight Ellison (Bob Gunton) is Trudy's father, a TV game show producer.

Marcia Ellison

Marcia Ellison is Trudy's mother. She states in "Mr. Monk and the Game Show" that she could not bring herself to enter Trudy's bedroom for two and a half years after her death.

Gail Fleming

Gail Fleming (Amy Sedaris) is Sharona's younger sister and an actress. She first appeared in "Mr. Monk and the Earthquake", where Sharona, Benjy and Monk stay at her house after a small earthquake. Her second appearance was in "Mr. Monk Goes to the Theater". In this episode, she is framed by her understudy for stabbing someone in a play. In "Earthquake" she remarks to Sharona that she thinks Sharona copies her (moving to San Francisco, buying the same purse, etc.).

Cheryl Fleming

Cheryl Fleming (Betty Buckley) is the mother of Sharona and Gail Fleming. When her husband, Douglas, died, she was left to raise two kids alone. She visits Sharona in "Mr. Monk Goes to the Theater", just when Gail is framed for murder. She then begs Monk to take the case, which he eventually does, though reluctantly. She thinks Sharona is the detective with Monk as her assistant.

Linda Fusco

Linda Fusco (Sharon Lawrence) is Leland Stottlemeyer's ex-girlfriend and a real estate dealer. The two began dating shortly after she hired Monk to investigate damages to her car in "Mr. Monk, Private Eye," and she even sets Stottlemeyer up with a new apartment. The two continued to see one another, but their dates were often interrupted, postponed or cancelled as a result of Stottlemeyer's duties. She resorted to bidding on a date with him at a bachelor auction just to get him alone in "Mr. Monk and His Biggest Fan". The relationship ended after Monk proved her the murderer of her former partner in "Mr. Monk and the Bad Girlfriend," leaving Stottlemeyer to wonder if the relationship was real or merely something she'd planned from the beginning. At the end of the episode, he tosses something into the ocean, saying "It's only a rock," suggesting that he was going to propose to Linda while in Hawaii.

Trevor Howe

Trevor Howe (Frank John Hughes and David Lee Russek) is Sharona's ex-husband and Benjy's father from New Jersey. He appeared in two episodes: "Mr. Monk and the Sleeping Suspect" and "Mr. Monk and the Girl Who Cried Wolf". In "Mr. Monk and the Sleeping Suspect", he shows up at Sharona's house for Benjy's birthday, seemingly a "different man." Benjy is happy to have a father, which is one of the reasons Sharona decides to quit being Monk's assistant and move back to New Jersey with Trevor. She later discovers, however, that he got plane tickets to where his rich uncle lives since his uncle cut him off when he got divorced. In his next appearance, Sharona asks Trevor to take Benjy, afraid she is losing her sanity. In "Mr. Monk and the Red Herring," it is revealed that he has re-married Sharona. In the episode, "Mr. Monk and Sharona" Sharona reveals that they have broken up for good. He re-appears in the novel Mr. Monk and the Two Assistants, having been framed for murder.

Trudy "T. K." Jensen

Trudy "T. K." Jensen (Virginia Madsen) is Captain Stottlemeyer's love interest in season 8. She is set to appear in a three-episode story arc, beginning with "Happy Birthday, Mr. Monk". She works for a magazine like Consumer Reports and was covering the debut of the new Self Cleaning Vacuum. Throughout the episode Leland was trying to figure out what her nickname T.K. stood for, but when he found out that her first name is Trudy he suggested that T.K. was fine. In the episode "Mr. Monk is the Best Man", she marries Capt. Stottlemeyer after they have been dating for 6 months. Monk is shown to have been fine that her name is Trudy, believing everyone should have a Trudy in their life.

Harold Krenshaw

Harold J. Krenshaw (Tim Bagley) is another patient of Dr. Kroger (and later Dr. Bell) who also suffers from obsessive-compulsive disorder. Despite sharing the same disorder, Harold and Adrian are constantly at odds, mostly over which of them is liked better by Dr. Kroger, or which of them have made more progress in overcoming their various problems. In addition to his OCD, Harold also suffers from acute paranoia and narcissism. As a result, he deludes himself that everyone is out to get him, either because of his importance in the scheme of things, or because he inspires outrageous jealousy in everyone else. He often takes great pleasure in "getting" other people before they get him, especially Monk.

Harold is married and has a son, Jimmy.

Harold first appeared in "Mr. Monk and the Girl Who Cried Wolf" when he and Monk bicker over the arrangement of magazines in Dr. Kroger's waiting room.

In "Mr. Monk and the Election" Harold won (against Natalie Teeger) to become a member of Julie's school board.

In the episode "Mr. Monk Gets a New Shrink," Harold takes a bullet to save Dr. Kroger's life (much to Adrian Monk's dismay).

In "Mr. Monk and the Daredevil," Harold eclipses a jealous Monk in fame when the public at large believes him to be a notorious Human Fly known only as The Frisco Fly. In reality, Harold was dropped into the role by his cousin who was trying to kill him over an inheritance. Unaware of the murder plot, Harold went along with the charade because he loved the public attention, getting a golden opportunity to infuriate Monk, and gaining new respect and admiration from his son.

In "Mr. Monk and the Buried Treasure," Monk agrees to help Dr. Kroger's son Troy decipher what appears to be a treasure map in an attempt to once more out-do Harold, who has just given the gift of a wristwatch to their therapist.

In "Mr. Monk Gets Hypnotized," following the death of Dr. Kroger, Harold tries hypnotic regression therapy with a new doctor (played by Richard Schiff) which at first seems to cure him of his OCD, inspiring Adrian to try it as well. However, the therapy later backfires when Harold's feelings of euphoria lead him to take off all his clothes in public, and he is arrested for indecent exposure.

Harold made a brief cameo appearance in "Mr. Monk's 100th Case," as a talking head on a television special commemorating Monk's achievements as a detective, which Harold derided.

Harold also appeared in the seventh season finale, "Mr. Monk Fights City Hall." Now serving on the San Francisco City Council, Harold gleefully votes against Monk's motion to preserve the parking garage where Trudy Monk was murdered, instead of demolishing it to build a children's playground. At first, Monk sways the a majority of the council to vote in his favor, but inadvertently tips the vote when he insults one of the other council members while exposing a murderer. Harold also (thanks to an inadvertent slip from Natalie) learns the name of Monk's new therapist, Dr. Bell, whom Adrian has been bragging about, and announces that he will also be seeing Dr. Bell in the future.

Harold briefly appeared in the eighth season episode, "Mr. Monk is Someone Else," when Monk goes to Los Angeles masquerading as a mob hit man. Harold, who happens to be visiting Los Angeles, calls out to "Adrian," but Monk stays in character and tells Harold he has the wrong man, eventually threatening him with immediate death if he doesn't go away.

In his latest appearance, "Mr. Monk Goes to Group Therapy", Monk finds himself sharing group therapy sessions with Harold when his HMO refuses to compensate him for any more individual sessions with Dr. Bell. The two butt heads constantly, even to the point that when two of their other group members are killed under mysterious circumstances, Harold accuses Monk of being the killer. Both men are ultimately kidnapped by the real killer and thrown into a car trunk together, where they both break down with claustrophobia and finally become friends: Harold admits that he has greatly exaggerated his own progress to goad Adrian, while Adrian admits that he envies Harold's relative success in going on with his life despite his many fears. The two men realize that they share many of the same problems, and even overcome their claustrophobia together when Monk convinces Harold to see the trunk as a protective space rather than a trap.

Afterwards, in an extraordinary gesture, Harold voluntarily transfers to another psychiatrist, to let Monk's "group sessions" with Dr. Bell be individual sessions after all.

Marci Maven

Marci Maven (Sarah Silverman): originally an obsessive fan of TV star Brad Terry in "Mr. Monk and the TV Star" until Monk revealed he murdered his ex-wife. She returns in "Mr. Monk and His Biggest Fan". In that episode, she found a new object to obsess over: Monk. She goes as far as paying $800 for him, buying him for six hours. The next day, she shows him how much she loves him, wearing his old pants, serving his drink in his old glass, even showing him a diorama of them from "Mr. Monk and the Three Pies", while singing him a song on her guitar about him. She loses interest by the end of the episode when she is shot at in a lumberyard by the man who framed her dead dog for the murder of his wife. She gives him a package holding all his stuff she took, saying her new obsession, F. Murray Abraham ("May God have mercy on his soul," Monk tells Natalie) "wouldn't understand." However, she reappears in "Mr. Monk's 100th Case", interviewed in a television show, reverting once again to her obsession with Monk. At one point, she stated, "I'm not crazy, just a fan." Coincidentally, Monk said the exact line to his favorite actress in "Mr. Monk's Favorite Show".

Karen Stottlemeyer

Karen Stottlemeyer (Glenne Headly) is the environmentally-conscious ex-wife of Leland Stottlemeyer and mother of their two children, Jared and Max. She also films documentaries. She first appeared in "Mr. Monk and the Very Very Old Man", where she begged her then husband to investigate the death of an old man. She later appears in "Mr. Monk and the Captain's Wife", where she is temporarily put in a coma after being hit by a tow truck in her car; "Mr. Monk Gets Fired", where she films a documentary of the San Francisco Police Department; and "Mr. Monk and the Captain's Marriage", where Leland believes she is having an affair. It is revealed she was actually seeing a divorce lawyer. She has a sister.

Mitch Teeger

Lieutenant Commander Mitch Teeger is Natalie's late husband who was a Navy fighter pilot. He died in the Kosovo War and he allegedly abandoned his men, but, as revealed by Natalie in "Mr. Monk and the Election," she doesn't believe the reports.