On Jan. 11, 1999, Jon Stewart took over The Daily Show from Craig Kilborn. It was different times, a different set, and Stewart's suit didn't quite fit right. The topic was the upcoming impeachment trial of then-President Bill Clinton, and Stewart was as hard on Clinton as his Republican prosecutors. And man, he looks young. If you want to see how young Stephen Colbert looked in 1999 (eerily the same), you can watch his segment on the same show, about selling Clinton impeachment memorabilia. For a look at Stewart's Daily Show debut, on the night he announced his retirement, watch below. —Peter Weber
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