These interviews will make you cringe harder than a root canal… Join us as we count down our picks for the most uncomfortable and unsettling late night talk show moments! Our countdown includes Madonna dropping f-bombs, Letterman making celebrities cry, inappropriate touching, and hosts crossing lines that should never have been crossed. From Andy Dick’s inappropriate behavior with Ivanka Trump to Letterman sucking Jennifer Aniston’s hair, these moments shocked viewers and left lasting impressions. We also explore how hosts like Jimmy Fallon normalized controversial figures and Jay Leno made homophobic jokes that forced apologies. What disturbing moments from late night interviews live rent-free in your head? Let us know in the comments!
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