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20 Years of Watercooler Moments

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Tom Selleck, Rosie O'Donnell

Evan Agostini/Getty Image; Joe Kohen/WireImage

Rosie O'Donnell Ambushes Tom Selleck

Whodathunk an NRA TV ad pitchman would get ambushed by a show-tunes-spewing chat host? But Rosie cornered Tom into debating assault weapons in the wake of Columbine in 1999. To his credit, Tom didn't run for cover while both of them tried to keep it civil. Rosie's been in the cross-hairs of the right wing ever sense.

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Conan O'Brien, Chelsea Handler

E! NEWS NOW, KATE MIDDLETON, PRINCE WILLIAM, KIDS, PHOTOS

Kim Kardashian

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