After the "The Dana Carvey Show" was canceled, Stephen Colbert looked for work for a solid year with little success. He failed to get a correspondent gig with "Good Morning America" (NBC, 1975-2004), then appeared in a single episode of "Spin City" (ABC, 1996-2002), before spending a brief time writing for "SNL." The rest of the 1996-97 period was spent worrying about how to feed his family and pay the rent.

Then out of the blue, he was offered a job on "The Daily Show," then hosted by Craig Kilborn. Without ever having watched the show, Colbert accepted the job. With the prospect of food and rent money looming on the horizon, Colbert began what would become his defining gig playing a pompous, ill-informed correspondent on a fake news program. Under Kilborn, "The Daily Show" had little to do with politics. But when anchor Jon Stewart took over in 1999, the show steered full boar towards political satire. Colbert had never thought much about his own political stance or doing political comedy but to his surprise, he soon discovered that he indeed had strong (and liberal) opinions on many issues.

Over the next six years, Colbert and company lacerated politicians, pundits and political wonks of all stripes. From the election debacle in 2000 through the subsequent debacle in 2004, "The Daily Show" became a safe haven from the inanity of politics and the 24-hour spin cycle that passed for TV news. But while "The Daily Show" considered itself a comedy show first, many who watched felt that the truth was more faithfully represented than on so-called real news shows. Meanwhile, Colbert honed his cocksure and idiotic correspondent character, adding considerable gravitas and diction to reports while simultaneously looking the fool. Such memorable moments included roving the floor at the 2004 Democratic National Convention (he badgered an avid listener of John Kerry's speech who turned out to be one of the speechwriters); filling in for an interview with Al Sharpton as Al Sharpton; and hosting a semi-weekly segment, "This Week in God," where Colbert walked the tightrope between comedy and religion.

During his stint on "The Daily Show," Colbert found time for other projects, as well. He made his feature debut as Happy Successful Guy in the independent romantic comedy, "Let It Snow" (1999). Also that year, Colbert and his Second City pals created "Strangers With Candy" (Comedy Central, 1999-2001), starring Amy Sedaris as a 46-year-old runaway/ex-con/former drug addict and alcoholic who returns home and attends high school as a freshman, drawing the wrong conclusions from her weekly crises. After appearing in episodes of "Curb Your Enthusiasm" (HBO, 2000- ) and "Law & Order: Criminal Intent" (NBC, 2001- ), he lent his distinguished voice to various characters on "Crank Yankers" (Comedy Central, 2001- ), "The Venture Brothers" (Cartoon Network, 2002- ) and "American Dad" (Fox, 2004- ). Meanwhile, "The Daily Show" became a cultural hit and critical success, earning several Emmy awards for Outstanding Variety, Music or Comedy Series and Outstanding Writing. The show also won a 2004 Peabody Award for journalism a first for a fake news show.

By 2005, Colbert felt that it was time to move on. He left "The Daily Show" in October and took his patented correspondent persona with him to start his own show, "The Colbert Report" (Comedy Central, 2005- ). Part Bill O'Reilly, part Lou Dobbs, with a smidgeon of Anderson Cooper, Colbert's cocky and clueless news anchor followed "The Daily Show" and became an immediate hit. Segments such as "Better Know a District," where he set out to interview 434 congressional representatives (disgraced Republican Duke Cunningham was off the list), and "The Word," where Colbert pontificated on topics a la Bill O'Reilly while on-screen graphics comically undercut his argument, became overnight staples. The first installment of "The Word" coined the word "truthiness," something he described as a devotion to information he wished were true, no matter the facts. Colbert even engaged in a mock-persecution of the Associated Press  again stealing a page from O'Reilly and his attacks on The New York Times -- accusing the wire service of not giving him credit for coining the word and calling them the biggest threat facing America.

Meanwhile, Colbert continued with other projects, including a feature version of "Strangers With Candy" (2005) which was purchased by Warner Independent Pictures at the 2005 Sundance Film Festival.