55 Chilling Late-Night Talk Show Moments

Late night talk shows are a wellspring of salacious discussions and witty banter. This is especially true when the show books a controversial or cutting-edge guest to appear on the show. These rule-breaking loose cannons provide for some of the most entertaining moments in television history, as this collection of photos reminds us. 

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Remember When Madonna Made Johnny Carson Blush Because of Her Late Night Flirting?

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When Johnny Carson hosted Madonna on The Tonight Show on June 9, 1987, he probably assumed he would simply be interviewing the rising pop singer, but Madonna had other plans. The sexy singer flirted shamelessly with Carson until it was obvious to television viewers that the late night host was totally smitten with the Bay City, Michigan, native. Just a few weeks after her inaugural Tonight Show appearance, Madonna embarked on a world tour to promote her “Who’s That Girl” album. Later that year, the “Like a Virgin” singer sought an annulment of her marriage to actor Sean Penn. The split was not because of her flirtation with Johnny Carson, but due to irreconcilable differences.