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30 most shocking moments in late night history

By Jeremy Dick

NEW YORK - FEBRUARY 11: Actor Joaquin Phoenix, waves to the audience during his interview with Late Show host David Letterman during the Late Show with David Letterman Wednesday Feb. 11, 2008 on the CBS Television Network. This photo is provided by CBS from the Late Show with David Letterman photo archive. (Photo by John Paul Filo/CBS via Getty Images)
NEW YORK - FEBRUARY 11: Actor Joaquin Phoenix, waves to the audience during his interview with Late Show host David Letterman during the Late Show with David Letterman Wednesday Feb. 11, 2008 on the CBS Television Network. This photo is provided by CBS from the Late Show with David Letterman photo archive. (Photo by John Paul Filo/CBS via Getty Images) /
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3. Conan O’Brien wastes NBC’s money for firing him

We all know about the NBC late night fiasco with Jay Leno and Conan O’Brien. To summarize it again real quick, Leno left The Tonight Show to start a new show, with O’Brien taking over hosting duties. When Leno’s new show tanked with O’Brien’s Tonight Show struggling to catch on, NBC panicked and wanted to put Leno back into his old slot when The Tonight Show aired. The decision was soon made to take Conan off the show, paying him millions of dollars just to leave.

But those wouldn’t be the only costs NBC had to pony up in the wake of Conan’s exit. Knowing he was on the way out the door, Conan figured he’d hit the network back right in the wallet by introducing skits that “weren’t so much funny” as they were very, very expensive.

The most infamous bit was when Conan unveiled a Bugatti, the most expensive car in the world, dressed up as a mouse. Playing in the background was a song by The Rolling Stones, whose licensing fees for their songs are basically astronomical. It was a hilarious way to get back at the network for the unfortunate Leno situation.

Next: 2. Crispin Glover is either crazy or on drugs

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