(Original Air Date: 10/29/98) Reese Witherspoon talks about 1950s fashion, working with Paul Newman, and the hazards of acting in New York.

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Running from 1993-2009, Late Night with Conan O’Brien is one of the most beloved late night shows in television history. Known for its absurdist humor, hilarious celebrity interviews and featuring the best stand-up comedians and musical acts of the ‘90s and early 2000s. Hosted by Conan O’Brien alongside sidekick Andy Richter and house band Max Weinberg and the Max Weinberg 7, Late Night with Conan O’Brien featured unforgettable segments like “If They Mated”, “In the Year 2000”, “Desk Drive”, and made a breakout star of Triumph the Insult Comic Dog.