|Parks and Recreation character|
|First appearance||"The Set Up"|
|Last appearance||"One Last Ride"|
|Portrayed by||Ben Schwartz|
|Occupation||Co-creator of Entertainment 720
Salesman at Lady Foot Locker
|Family||Mona-Lisa Saperstein (twin sister)
Dr. Saperstein (father)
Jean-Ralphio Saperstein is a fictional character played by Ben Schwartz in the American comedy television series Parks and Recreation. He is the cocky friend of Tom Haverford (Aziz Ansari) and, like Tom, believes himself to be a playboy and pickup artist, although he is looked upon with contempt by most people around him. He tries to dress stylishly and often speaks in slang terms. At the end of the third season, Tom leaves his city hall job to start an entertainment company with Jean-Ralphio.
Background and personality
Jean-Ralphio Saperstein (Ben Schwartz) is a cocky friend of Tom Haverford who, like Tom himself, fancies himself a pickup artist and baller, although he is looked upon with contempt by most people around him except Tom. He makes up and raps spontaneous rhymes and often speaks in slang terms such as variations of the suffix -izzle as popularized by rapper Snoop Dogg; for example, while comforting Tom at one point, Jean-Ralphio encourages him to "Turn that frizown upside-dizzity".
Jean-Ralphio is first introduced in "The Set Up", when Tom brings him in for an interview to be Ron Swanson's new assistant; he is quickly rejected. In "Woman of the Year", when Tom is trying to find investors to help him buy a share of the Snakehole Lounge nightclub, Jean-Ralphio contributes $5,000 of the $10,000 Tom needs. Unable to raise the rest, the two approach Donna Meagle about investing along with them, but after a sales pitch from Jean-Ralphio, Donna rejects them and tells Tom, right in front of Jean-Ralphio, "I hate that guy."
Jean-Ralphio also appeared in "The Master Plan", where April Ludgate flirted with him at the Snakehole Lounge to make Andy jealous, prompting Andy to say of him, "That Ralph Macchio guy's a total douche." Jean-Ralphio appears in "The Fight", where he helps Tom raise awareness for his new drink Snakejuice at the Snakehole Lounge. At one point, after a fight between Leslie and Ann, a drunken Leslie demands that Jean-Ralphio "dance up on me", to which he immediately and excitedly agrees.
In the third season finale, "Li'l Sebastian", Tom encourages Jean-Ralphio to start a multimedia entertainment company called Entertainment 720. After their first successful job organizing a memorial event for celebrity miniature horse Li'l Sebastian, Tom decides to quit his city hall job to work with Jean-Ralphio and the company, which opens a modern office with strange decor and completely stark-white walls. In the episode "Bailout", his sister Mona Lisa Saperstein (Jenny Slate) begins working for and then enters into a sexualized relationship with Tom Haverford.
In season 6, we meet Jean-Ralphio and Mona Lisa's father, Dr. Saperstein, an obstetrician played by Henry Winkler, who is often lied to by his children. Under the impression that Tom unfairly drove Jean-Ralphio out of their business and took Mona Lisa's virginity, Dr. Saperstein opens a similar apparel store across from Tom's store, Rent-a-Swag, in order to drive him out of business. In the episode "One Last Ride" Jean-Ralphio fakes his death along with Mona Lisa and tries to get insurance money to build a casino in Tajikistan. They get seen and run away to no one knows where. In the same episode you can see his name on a champagne that is being served to Craig and his husband, also in that episode it is revealed that he had been in love with Leslie for years. 
Schwartz originally met with Parks and Recreation co-creator Michael Schur to discuss playing a different role on the show, and Schur liked him so much that the character Jean-Ralphio was created specifically for him. Schwartz said the character had "just a couple of lines" at first, but was eventually expanded. After making his first few appearances in the second season, Schwartz began to appear less frequently because he was cast in the NBC action spy series Undercovers, but he was able to return more often after it was cancelled. Schwartz was cast in the Showtime series House of Lies, but Michael Schur said they hoped to have Schwartz back "early and often". Like other cast members, Schwartz improvises a great deal during filming.
In May 2011, Jean-Ralphio was placed number 7 on SplitSider's "The Ten Funniest Recurring Characters Currently on TV".
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