David Letterman Primetime Special: Iconic Bits, Awkward Moments, Divisive Feuds

A still from 'David Letterman: A Life on Television.'

Ray Romano hosted the look back at the 'Late Show' host's storied career.

CBS prepared to say goodbye to David Letterman with a primetime special that featured the legendary talk show host's most iconic moments, including Drew Barrymore flashing him, Justin Bieber revealing his limited art history knowledge, and Crispin Glover aiming a kick at his head.

David Letterman: A Life on Television was hosted by Ray Romano and aired Monday, celebrating the host's 33-year career in late-night. His final Late Show airs on May 20.

The special started with a medley of clips set to R.E.M.'s "It's the End of the World as We Know It (and I Feel Fine)." This segued into snippets of a number of memorable interviews, including Bieber referring to Michelangelo's masterpiece as the "Sixteenth Chapel" in 2012, Gillian Anderson making out with the host in 2002, and Madonna infamously dropping the f-bomb repeatedly in 1994.

The special highlighted Letterman's signature segments, including Stupid Pet Tricks and Stupid Human Tricks. A best-of Top Ten list ended in Betty White telling people that the secret to longevity is not to "waste your time watching this crap."

Other moments included Letterman running a McDonald's drive-thru in 1993, scenes with his various staff members over the years, and snippets of memorable music guests.

A lengthy segment focused on Letterman's apparent friction with Oprah Winfrey and his campaign to land her as a guest, an effort that finally came to fruition four years later and concluded with Letterman walking Winfrey to the Broadway opening night of The Color Purple, which she produced. 

Romano credited Letterman with launching his career, as Romano's 1995 stand-up spot on the Late Show led to Letterman producing Everybody Loves Raymond. Romano concluded the program by commending the host on his achievements, despite acknowledging that Letterman typically is not a fan of such "schmaltz."

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