In 1995, Quinn was hired by Saturday Night Live as a writer and featured player until 1997–1998 season, when he became a full cast member. He established himself on the show with characters such as "Lenny the Lion" and "Joe Blow", and did the recurring segment "Colin Quinn Explains the New York Times". Quinn took over as host of the Weekend Update segment in January 1998 after Norm Macdonald's firing, and anchored the segment until departing SNL in 2000. Quinn would often comment on the highly publicized media circuses such as Clinton-Lewinsky Scandal and the Microsoft Anti-Trust Trial. At the end of each Weekend Update segment, he would use the catchphrase, "That's my story and I'm sticking to it." He was not thrilled about his run on the show, declaring on an episode of Tough Crowd, "I don't miss it."
During his SNL years, Quinn made his Broadway debut in his one-man show, Colin Quinn: An Irish Wake co-written with fellow comedian Lou DiMaggio, and was offered the role of Scott Evil in Austin Powers: International Man of Mystery by Mike Myers, which he turned down to make time for his writing projects. The role was taken by Seth Green.
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“How vigilant we are! determined not to live by faith if we can avoid it; all the day long on the alert, at night we unwillingly say our prayers and commit ourselves to uncertainties. So thoroughly and sincerely are we compelled to live, reverencing our life, and denying the possibility of change. This is the only way, we say; but there are as many ways as there can be drawn radii from one centre. All change is a miracle to contemplate; but it is a miracle which is taking place every instant.”
—Henry David Thoreau (1817–1862)