Throughout the mid-1990s, Stephen Colbert had received a marginal amount of fame in the comedy world from his stint on “The Dana Carvey Show” and his time as a contributor to “Saturday Night Live.”

In 1997, Colbert was hired as a special correspondent on “The Daily Show,” and after several years became one of the program’s most beloved faces.

In a 1999 trip to “Whose Line Is It Anyway?,” Colbert showed off some of his best improv work and revealed a side of himself rarely seen on his politically oriented Comedy Central show.

Though each skit Colbert appeared in was funny, his rap with “Whose Line” star Wayne Brady stands out as one of Colbert’s finest moments.

Dressed in a suit that seemed a little too big for him, Colbert went toe to toe with Brady in an absurd round of comedy-rap.

Douglas Barclay is a Senior Editor at Rare. Follow him on Twitter @douglabarclay17
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