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|First appearance||"Diversity Day" (2005)|
|Created by||Greg Daniels
|Portrayed by||Paul Lieberstein|
|Occupation||Human Resources Representative, Dunder Mifflin, Scranton Branch|
Sasha Flenderson (daughter)
Kathy Becker (ex-wife)
Toby H. Flenderson is a fictional character on the U.S. comedy television series The Office. He is portrayed by Paul Lieberstein, who was also the show's writer, director, producer and showrunner. He is the human resources representative at the Scranton branch of the paper distribution company, Dunder Mifflin. Toby is an original character with no counterpart in the original British series. Many jokes about Toby revolve around his unrequited crush on coworker Pam Beesly, the animosity he faces from Scranton branch manager Michael Scott, and his increasingly desperate need for romance and validation.
Character creation and development
A fan of the original British comedy The Office, Paul Lieberstein was friends with writer/producer Greg Daniels who became one of the showrunners for the American version. This relationship led Paul to visit the set of The Office while its pilot was filming, and eventually be asked to join as a writer. In an interview for The Office Ladies podcast, Paul Lieberstein said "I had worked with Greg Daniels before and known him very long time, and we did King of the Hill together. And when they started the show, I stopped by the pilot. You know, I had nothing to do with the pilot, but I stopped by a few days and it was... I just kind of loved what was happening."
Joining the writing staff for the American version of The Office during its first season, Lieberstein was surprised that the writers and show's actors regularly discussed the stories and character evolution. Later on, Daniels decided to cast some of the show writers as supporting characters in the background of The Office, believing the experience could make them better writers for the show in the process. In his interview for The Office Ladies podcast, he said, "So there's this like kind of a very traditional thing that writers and actors are separated on a TV show... and they're kind of asked not to talk. [Greg Daniels] at this point was questioning a lot of those rules. 'Why was this happening and does this really make a better TV show?'... We talked about just doing a little thing to kind of have the experience of being an actor. And hopefully it would inform our writing. I'm not sure how Toby happened, but I feel like I left the room and I came back and they said, 'You're going to play this part.'"
Lieberstein was asked to play Toby Flenderson, the human resources rep for the Scranton branch of paper distributor Dunder Mifflin. Due to his position in HR, Toby has duties to ensure the company's procedures and rules of conduct are followed. As such, he is perceived as an enemy by lead character and Scranton branch manager Michael Scott, who constantly dismisses company procedure and rules of conduct in order to pursue fun and a personal relationship with his employees.
Lieberstein found playing the role of Toby challenging at first, not having much experience in acting. He remarked that he initially kept calling actors by their real names rather than their character names, and that he kept speaking too quietly because he was using the volume he would use in a private conversation and not thinking of the microphones needing to hear him clearly. He said that a breakthrough moment happened during a scene between him and actor Brian Baumgartner. "We were doing a kitchen scene and they kept telling me to speak up. And then Brian said, 'Why don't you imagine? Like, this room is artificially quiet because they turned off the refrigerator...Why don't you imagine that the refrigerator's on and you have to talk over it? And I was like, 'Oh, an actor does that...' They don't just do what feels real. They have to like find a way to do what they need to do and make it feel real."
Toby became a regular character throughout the run of The Office. Since Lieberstein was a writer on the show and couldn't regularly be on set, the character of Toby was depicted as working in the office annex, out of sight from the main part of the office where most scenes took place. Likewise, to excuse Lieberstein from appearing in some episodes, Michael's animosity towards Toby meant the HR representative was sometimes excluded from activities that otherwise involved most of the characters.
Along with being a constant target of Michael's (and then of Jim when he became an acting manager or co-manager), an ongoing joke regarding Toby was his crush on co-worker Pam Beesly, who initially is engaged to warehouse worker Roy Anderson and then later falls in love with and marries Dunder Mifflin salesman Jim Halpert. Just as he was often unable to stand up to Michael, Toby repeatedly found himself unable to express his feelings to Pam and panicked when he suspected his feelings were too obvious (unknown to him, Pam thought he was cute and hoped they could talk more as friends). Toby became resentful of Jim and his relationship with Pam. Other recurring jokes revolved around his desire but seeming inability to enjoy and possibly retire in Costa Rica, his unhappy (and possibly abusive) marriage that led to divorce, his desire to be a mystery novelist, his time as a juror on the Scranton Strangler case which then led to his temporary obsessive fear that the convicted man was actually innocent, and his brief sexual relationship with character Nellie Bertram, a relationship he romanticized and obsessed over for some time. Despite being the butt of many jokes and having no deep friendship with anyone in the show, the final episode showed Toby's co-workers reaching out to show him his presence was appreciated.
Toby's brother Rory was played on the show by Paul Leiberstein's actual brother.
Fictional character biography
According to a deleted scene from the episode "Launch Party", Toby Flenderson is colorblind. Toby is also allergic to mushrooms ("Survivor Man"). In his childhood, Toby's parents get a divorce and pressure him to choose between them. Toby also has a brother named Rory, but it is not made clear how the divorce affected him. Later, Toby attends Bishop O'Hara High School and Penn State University. In the episode "Casual Friday", a diploma reveals Toby has a B.S. in psychology from California Coastal College. The episode "Counseling" reveals he has a degree in social work from Temple University. His brother Rory eventually moves to Boulder, Colorado.
At some point, Toby lives in Honolulu for a year. He also attends seminary for a year but drops out when he meets Kathy Becker and falls in love. The two marry, move to Scranton, and have a daughter named Sasha. Toby's marriage is eventually unhappy and he indicates in one episode that it was also physically abusive. The marriage ends in divorce, after which Toby repeatedly seeks to prove his worth and love to his daughter, fearing that she thinks of her mother as a hero and not him (as said in "Moroccan Christmas"). The episode "Hot Girl" establishes that, during the separation or after the divorce, Toby briefly lives in his car.
"Local Ad" establishes that Toby works in advertising for three years before losing that job. Needing a new job and not caring much what it is, Toby applies to be an HR representative at Dunder Mifflin, despite having "no passion" for such work. As an employee of the Scranton branch, he mostly stays at his desk in the office annex, rarely showing signs that he desires to socialize but getting along with most co-workers. He repeatedly shows signs of low self-esteem and a reluctance to enforce policies and codes of conduct he feels should be obvious to common sense. When branch manager Michael Scott repeatedly violates company policy and conduct, Toby points this out but will often relinquish when Michael continues to defy him, unless he sees a major legal situation or enough employees pressure him to contact the corporate office. Rather than sympathize that Toby is doing his job by enforcing these policies, Michael sees him as an enemy who is making a personal effort to spoil fun. As Michael puts it, "Toby is in HR, which technically means he works for corporate, so he's really not a part of our family." With the other co-workers, Toby is often reluctant to take serious action with inner-office conflicts, preferring instead that employees vent about their problems but then resolve the situations themselves. Not wishing to draw attention to the branch and believing that Jim Halpert's pranks are harmless, Toby lies to employee Dwight Shrute when he says he sends all of Dwight's complaints about Jim to the corporate office.
Despite Michael's treatment of him, Toby offers kindness during some occasions when Michael seems depressed and alone, such as in "The Deposition" and "Niagara." During a counseling session with Michael, Toby comes to learn about his childhood and gains a greater understanding of him. This only causes deeper resentment from Michael. In "The Lover," Toby is delighted when Michael indicates positive feelings towards him (though this turns out to be a ruse) and remarks that he believed and hoped "Michael would like me once he got to know me." In "Goodbye, Michael," Michael prepares to relocate to Boulder, Colorado. Learning this, Toby suggests Michael could meet and possibly befriend his brother Rory who lives in Boulder, then encourages Rory to seek Michael out. Despite his overall hope that they could be friends, Toby is hurt by Michael's behavior and at times angry and resentful. In "Double Date", when Pam is told she's allowed to punch Michael as hard as she wants, Toby instructs Pam on how to punch with even greater force.
Toby's lack of passion for his job turns into increasing resentment and depression regarding his circumstances and occasional bouts of bad luck. He regularly hopes to one day move to Costa Rica and enjoy retirement there. A quiet, introverted man, he feels overwhelmed at times by his cubicle being next to the very chatty customer service agent Kelly Kapoor. His discomfort increases when Kelly's on-again, off-again boyfriend Ryan is made her cubicle mate, leading to regular arguments and flirtations between the two. Toby later remarks that he doesn't think Michael put Ryan in the same cubicle as Kelly so their behavior would torture him, but adds that if this was the goal then it was a genius move.
At some point, Toby develops a crush on Scranton branch secretary Pam Beesly, though she is engaged to warehouse worker Roy Anderson, whom she has dated since high school. After a near decade of dating and several years of an engagement, Pam is drawn to sales rep Jim Halpert who one day expresses he also has romantic feelings for her. When Pam says she still intends to marry Roy, Jim transfers to another branch of Dunder Mifflin. Soon afterward, Pam breaks off her engagement to Roy, realizing how hurt she is by Jim's departure. Months later, during "The Convention", Toby finds out that Pam is ready to date again. He makes a couple of attempts to ask her out but can't say the words. On other occasions, he tries to impress her with actions or arrange a situation where they will talk, hoping a romantic interaction will happen naturally, but it never does. In "Cocktails", Toby spends his whole evening trying to win a toy duck that Pam remarked was cute. When he finally wins and brings it to her, he is disappointed that Pam casually suggests he could give the duck to his daughter, and then says she had been hoping the two of them could talk but he was missing the entire evening. In a deleted scene for the same episode, Pam remarks Toby often looks like he wants to tell her something. Toby then attempts to explain how difficult his divorce was and that he has feelings for her, but Pam becomes distracted by a realization and leaves.
Months later, Jim (who has since returned to the Scranton branch) and Pam begin dating. In "Dunder Mifflin Infinity", seeing the two share a kiss in the break room, Toby realizes they are together and resents it. He sends out a memo asking for no public displays of affection in the office, admitting when asked that the memo is a response to Jim and Pam. The office is excited to hear the two are together and Pam wrongly concludes that Toby's memo was a joking way of congratulating the happy couple. When Jim and Pam ask if they need to fill out a company form indicating they are in a relationship, a resentful Toby first suggests that they don't need to if they're not seriously dating, then says they should just wait to fill out the form later (not wishing to make the relationship official on paper and clearly hoping Jim and Pam break up). Toby's resentment towards Jim and hope for his own romance with Pam continues in different episodes, such as in "Niagara" when he is happy by an implication that Jim and Pam are not coming to their own wedding and then looks disappointed when they do in fact show up.
On occasion, Toby's resentment about the relationship leads to criticisms towards Jim in "Did I Stutter?" and "Branch Wars." Overall, however, he maintains a decent relationship with Halpert and eventually seems to get over his jealousy, though he remains depressed at not finding true romance himself.
In the episode "Night Out", Toby puts his hand on Pam's leg and leaves it there for a long, awkward moment, which is noticed by several people, including Pam and Jim. Realizing what he has done, Toby tries to deflect attention from the act by abruptly announcing he's decided to leave Dunder Mifflin and move to Costa Rica. He then runs outside to the security fence, scales it, and disappears before further questions can be asked. At the end of season four, Toby follows through on his declaration and leaves Dunder Mifflin, replaced by Holly Flax who becomes Michael's love interest. In the two-part opener of season five, it is revealed that Toby suffered a serious zip-line accident on his third day in Costa Rica, resulting in a broken neck and spending months in traction at a hospital. In a talk with Oscar, he implies he is attracted to a woman who visiting a nearby resort with her husband, continuing his habit of desiring unavailable women. In a deleted scene from Baby Shower, Toby can be heard on the phone with his HR replacement Holly, noting he enjoys his stay at the hospital more than his treatment from Michael. Holly later relocates to a different branch. In "Frame Toby", it is revealed that Toby returns to his old job in Scranton and is there for a week before Michael notices.
Dunder Miflin is later bought by the company Sabre, and in "Whistleblower", Sabre CEO Jo Bennett discovers Toby is writing a mystery novel (which she also indicates it is not very good). In a deleted scene for "Nepotism", Toby reveals he has finished and self-published his book, only to be sued for plagiarism after his first four sales. Throughout the show's final seasons, Toby repeatedly brings ups his new self-published mystery novels to the office, all of which star his character "Chad Flenderman."
In "Classy Christmas", Toby has to go on leave so he can report for jury duty and is temporarily replaced by Holly again. The case turns out to be that of the Scranton Strangler. The suspect is found guilty and convicted. By the time Toby returns to the office, Holly and Michael have decided to get married and move to Boulder, Colorado, where Holly's parents live. In "Michael's Last Dundies", Toby reveals he has doubts about the verdict, saying he thinks the convicted suspect might be innocent. Soon afterward, in "Goodbye, Michael", Toby suggests Michael could befriend his brother Rory, who lives in Boulder.
Toby becomes increasingly obsessive in proving the innocence of the man convicted of being the Scranton Strangler, and visits the convict in the hopes that not only will he get more answers but the two may develop a friendship (Toby remarks this would be his first real friendship). When the convict attempts to strangle Toby, the HR rep realizes the man is in fact the real killer.
Another example of Toby's obsessive behavior revolves around Nellie Bertram, whom he meets in "Get the Girl." Their relationship is professional until "Dwight Christmas", when Nellie asks Toby about the Scranton Strangler case. After he bores her for several hours, Nellie finally leans in close to shush him. A puzzled Toby then asks if she is about to kiss him and, attempting to save face, Nellie does so. In "Customer Loyalty", Toby is affectionate towards Nellie and under the impression they are now in a relationship, while Nellie has forgotten the kiss and finds the affection awkward. Nellie later firmly establishes that there is no romantic connection between them, criticizing Toby as a loser (though she does admit to finding his meeting with the Scranton Strangler to be a brave act).
In the series finale, Toby is fired by corporate after Dwight was made branch manager of the Scranton office. Toby moves to New York where he lives with six roommates and continues his efforts to be a successful novelist. At the office reunion, he admits his life feels meaningless now that he is not being filmed for a documentary series. At Dwight and Angela's wedding, he breaks down crying when he dances with Pam, remarking that he is saddened by "everything." He is later cheered a little when his former co-workers insist he join them for post-wedding festivities.
In a "Where Are They Now?" photo gallery released by NBC, it's revealed Toby later takes an HR position at a TJ Maxx store.