Uncomfortable Moments That Aired On Ellen

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Ellen DeGeneres is hilarious, warm, and undeniably charming on her daytime talk show, The Ellen Degeneres Show, which has been on the air for more than 15 years. Her sweet nature puts her guests at ease, even when she asks them uncomfortable questions about their dating lives or pregnancy status. Unfortunately, not even DeGeneres' quick wit, humor and laid-back demeanor could salvage these awkward moments. From a thieving audience member to a Kanye West rant to a bizarre misunderstanding with Ryan Seacrest, some of these segments are more cringe-worthy than comical...
Kanye West | 0:33
Jessica Simpson | 1:34
Caitlyn Jenner | 2:40
Katy Perry | 3:42
Nicole Kidman | 4:24
"Ellen jail" | 5:43
Ryan Seacrest | 6:32
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