Watch: Bill Maher's awkward exchange with Don Lemon prompts Caitlyn Jenner to blast ex-CNN anchor as privileged, wealthy, entitled

A strange interaction on "Real Time with Bill Maher" prompted transgender celebrity Caitlyn Jenner to criticize Don Lemon as privileged, wealthy, and entitled.

On the most recent episode of "Real Time with Bill Maher," Lemon appeared alongside Scott Galloway – professor of marketing at NYU's Leonard N. Stern School of Business.

The trio were discussing the pro-Palestinian protests at college campuses around the country and how they force students to deal with "discomfort."

Bill Maher quipped about the student's discomfort, "You mean like living in a tent?"

The audience laughed at Maher's joke.

Lemon claimed, "I'm different than you guys. I'm a black gay man, so I live in uncomfortable spaces all the time."

Maher asked, "What's going on? Uncomfortable spaces?"

Lemon replied, "Look, I'm often the only person of color in the room."

Maher then joked, "There's only three of us here, come on."

The crowd then laughed.

Caitlyn Jenner applauded Maher for calling out Lemon and also slammed the ex-CNN anchor as "entitled."

Jenner wrote on the X social media platform, "Good on you Bill Maher Don is a privileged, wealthy, (not to mention entitled ie. Demands to X and CNN in alleged contract terms), celebrity. Get over yourself."

Lemon had a very short partnership with the X social media network to air "The Don Lemon Show." However, Elon Musk canceled the partnership after the first episode aired.

"X is a platform that champions free speech, and we’re proud to provide an open environment for diverse voices and perspectives," the social media network announced. "'The Don Lemon Show' is welcome to publish its content on X, without censorship, as we believe in providing a platform for creators to scale their work and connect with new communities."

X officials did not explain the reasoning for the dissolution of the relationship, only saying that "like any enterprise," they "reserve the right to make decisions" about business partnerships.

Lemon allegedly had a long list of demands in the partnership with X, including a free Tesla Cybertruck, a $5 million upfront payment on top of an $8 million salary, and a private jet trip to Las Vegas with his husband in exchange for hosting his show exclusively on X. Lemon also purportedly commanded an equity stake in the multibillion-dollar company and the right to approve any changes in X policy as it relates to news content.

Lemon was previously fired from CNN in 2023 after he began having divisive moments on the air. Lemon had a tense confrontation about race with former Republican presidential candidate Vivek Ramaswamy. He also ruffled the feathers of his "CNN This Morning" co-hosts Poppy Harlow and Kaitlan Collins when the 58-year-old host claimed that 51-year-old Nikki Haley was not "in her prime."

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