Ellen’s most uncomfortable on-air moments

Ellen’s most uncomfortable on-air moments

Ellen DeGeneresGetty Images
Blake Edwards

Ellen DeGeneres is incredibly charming, warm, and funny 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 things like their dating lives or whether or not they’re pregnant. It also makes it much easier to forgive her when she scares the daylights out of her guests onstage, backstage and everywhere else she can. DeGeneres is just so friendly and lovable that even when she’s being a little shady, you can’t help but get behind her.

Unfortunately, not even DeGeneres’ quick wit, humor and laid-back demeanor could salvage these awkward moments. From Kanye West’s seemingly endless raving to Jessica Simpson’s incoherent babbling, and from Ryan Seacrest’s bizarre misunderstanding over a bingo marker to a thieving guest and an ungrateful college student, some of these segments are more cringe-worthy than comical.