Shortly thereafter, he was hired to perform with Second City's touring company, initially as an understudy for Steve Carell. It was there he met Amy Sedaris and Paul Dinello, with whom he often collaborated later in his career. By their retelling, the three comedians did not get along at first—Dinello thought Colbert was uptight, pretentious and cold, while Colbert thought of Dinello as "an illiterate thug"[23]—but the trio became close friends while touring together, discovering that they shared a similar comic sensibility.[18]
When Sedaris and Dinello were offered the opportunity to create a television series for HBO Downtown Productions, Colbert left The Second City and relocated to New York in order to work with them on the sketch comedy show Exit 57.[18] The series debuted on Comedy Central in 1995 and aired through 1996. Despite only lasting for 12 episodes, the show received favorable reviews[24][25] and was nominated for five CableACE Awards in 1995, in categories including best writing, performance, and comedy series.[26]
Following the cancellation of Exit 57, Colbert worked for six months as a cast member and writer on The Dana Carvey Show, alongside former Second City cast mate Steve Carell, as well as Robert Smigel, Charlie Kaufman, Louis C.K., and Dino Stamatopoulos, among others. The series, described by one reviewer as "kamikaze satire" in "borderline-questionable taste," had sponsors pull out after its first episode aired, and was canceled after seven episodes.[27] Colbert then worked briefly as a freelance writer for Saturday Night Live with Robert Smigel. Smigel also brought his animated sketch The Ambiguously Gay Duo to SNL from The Dana Carvey Show; Colbert provided the voice of Ace on both series, opposite Steve Carell as Gary. Needing money, he also worked as a script consultant for VH1 and MTV, before taking a job filming humorous correspondent segments for Good Morning America.[18] Only two of the segments he proposed were ever produced, and only one aired, but the job led his agent to refer him to The Daily Show's then-producer, Madeline Smithberg, who hired Colbert on a trial basis in 1997.[28]
Strangers with Candy was conceived of as a parody of after school specials, following the life of Jerri Blank, a 46-year-old dropout who returns to finish high school after 32 years of life on the street. Most noted by critics for its use of offensive humor, it concluded each episode by delivering to the audience a skewed, politically incorrect moral lesson.[29] Colbert served as a main writer alongside Sedaris and Dinello, as well as portraying Jerri's strict but uninformed history teacher, Chuck Noblet, seen throughout the series dispensing inaccurate information to his classes. Colbert has likened this to the character he played on The Daily Show and later The Colbert Report, claiming that he has a very specific niche in portraying "poorly informed, high-status idiot" characters.[12] Another running joke throughout the series was that Noblet, a closeted homosexual, was having a "secret" affair with fellow teacher Geoffrey Jellineck despite the fact that their relationship was apparent to everyone around them. This obliviousness also appears in Colbert's Daily Show and Colbert Report character.
Thirty episodes of the series were made, which aired on Comedy Central in 1999 and 2000. Though its ratings were not remarkable during its initial run, it has been characterized as a cult show with a small but dedicated audience.[30] Colbert reprised his role for a film adaptation, which premiered at the Sundance Film Festival in 2005 and had a limited release in 2006. The film received mixed reviews. Colbert also co-wrote the screenplay with Sedaris and Dinello.[31]
Colbert lives in Montclair, New Jersey, with his wife Evelyn McGee-Colbert, who appeared with him in an episode of Strangers with Candy as his mother. She also had an uncredited cameo as a nurse in the series pilot, along with a credited one (as his wife, Clair) in the Strangers with Candy movie. McGee-Colbert actually met Jon Stewart, later a good friend of Colbert, before she met her husband in 1990. McGee-Colbert is the daughter of prominent civil litigator in Charleston, Joseph McGee, of the firm Buist Moore Smythe McGee. The couple have three children: Madeline, Peter, and John, all of whom have appeared on The Daily Show.[75] Colbert prefers, however, that his children not watch his show, The Colbert Report, saying, "Kids can't understand irony or sarcasm, and I don't want them to perceive me as insincere."[15]