Chelsea Handler’s Most Awkward Moments With Rappers

It's no secret that talk show host Chelsea Handler has a big appreciation for rappers. She made that clear yesterday during her interview with Pusha T when she said, "I have chemistry with rappers...cause I think black guys get me more than white guys." That chemistry has led to a number of ridiculous moments on her show and even to a short-lived fling with G-Unit's 50 Cent. But it's also led to some pretty awkward moments, including during last night's show, when she questioned why Pusha, at age 36, doesn't have kids or hasn't been married yet. XXL compiled some of these moments and put them in a list.

Chelsea calls Drake a "flaming homosexual" (1:13 mark)

On Drake's first appearance on Chelsea's show, she comments on how his drink of choice is wine spritzer and how that could mean that he plays for the other team, to which he awkwardly replies, "That's not how we want to start this."

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Chelsea spreads her legs For T.I. (1:02 mark)

For anyone who's watched her show, it's obvious that Chelsea has a gift for making her guests feel uncomfortable. She wasted no time doing that with T.I., who she jokingly opened her legs for after only a minute of talking.

Leaning back with Fat Joe (1:15 mark)

Fat Joe was the very first guest rapper on Chelsea's show back in 1998 (or, as Chelsea put it, he "popped" her rapper "cherry"). The episode was notable for a number of reasons, including for Joe's swipe at 50 Cent. But it was also memorable for the horribly awkward moment when Chelsea tried to do the "lean back" dance with Joe. She admits in the clip that she's a bad dancer, and we have to agree.

Chelsea and 50 Cent flirt over subject of vampires (3:01 mark)

These two eventually ended up dating for a bit, and it's easy to see why; on his first appearance on the show, they flirted constantly. It got uncomfortable when they were on the subject of Twilight, and Chelsea accused 50 of being a vampire. He replied by lifting his eyebrows at her and biting his lip. At that moment, somewhere in the world, Vivica Fox got angry.

Lil Jon asks Chelsea if she pops her pussy (3:58 mark)

It's not always Chelsea making rappers feel uncomfortable—sometimes it's the other way around. That was the case when crunkster Lil Jon was on the show. When talking about a song on his new album, he asked Chelsea a question that 2 Live Crew's Uncle Luke would have been proud of.

Common asks Chelsea if she likes black men (1:30 mark)

Chelsea's reply was, "It depends. There's a time of year in which I'm very interested in black men...It happens to be right around the holidays."

Big Boi, Lil Jon and Rick Ross talk about hitting it from the back (2:34 mark)

During the show's first-ever "rapper roundtable," things quickly get out of hand and lead to all three rappers talking about their favorite sexual position. At one point, Big Boi starts talking about the "ripples of her ass," and the word "awkward" just doesn't do it justice anymore.

Pharrell grabs Chelsea's ass