Colbert was born in Washington, D.C., the youngest of 11 children in a Catholic family. He spent his early years in Bethesda, Maryland. He grew up on James Island, South Carolina. Colbert and his siblings, in descending order by age, are James III, Edward, Mary, William, Margo, Thomas, Jay, Elizabeth, Paul, Peter, and Stephen.

During the same period, Colbert worked again with Sedaris and Dinello to develop a new comedy series for Comedy Central, Strangers with Candy. Comedy Central picked up the series in 1998 after Colbert had already begun working on The Daily Show. As a result, he accepted a reduced role, filming only around 20 Daily Show segments a year while he worked on the new series.  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. Colbert served as a main writer alongside Sedaris and Dinello, and portrayed 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. 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 Strangers with Candy 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. 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.

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