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"Damn!": The Best Hart to Heart Moments From Seasons 1 and 2

Kevin Hart has had a lot of funny and interesting moments with his guests on Hart to Heart. Here are just some of the very best ahead of Season 3.

By Tyler McCarthy

Kevin Hart’s original talk show Hart to Heart is about to drop Season 3 on July 6 (the comedian’s birthday), promising more deep conversations with celebrities, funny moments and, of course, a few gaffes from the host. 

With stars like Bill Maher, Dr. Dre, Dwayne Johnson, Issa Rae, J.Cole, John Cena, Mark Cuban, Sofia Vergara, Will Ferrell, and Will Smith ready to take the hot seat next to Hart, there’s a lot to look forward to in Season 3. However, it may also prompt some people to want to take a look back at some of the best moments to happen on the show in Seasons 1 and 2. Fortunately, we’re here to help. 

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For 22 episodes, Hart has sat down with some of the biggest names in Hollywood for a free-wheeling discussion where seemingly nothing is off limits. To help people get excited for even more from Hart to Heart, below is a rundown of just some of the best moments from the show so far. 

Don Cheadle’s Age Causes An Outburst

Even cursory fans of Hart to Heart have likely seen the viral clip of Hart reacting to Cheadle casually revealing his age in what he thought was a safe space. However, upon hearing that the Oscar and Emmy-nominated actor was 56 at the time, the host let slip a loud and somewhat disrespectful “damn!”

Cheadle was clearly a little annoyed so Hart playfully tried to play off his outburst as a showing of respect for the actor’s career, health and accomplishments…. But Cheadle isn’t stupid and therefore wasn’t buying it. What ensued was one of the most hilarious exchanges in the show’s history. The moment became so famous that even Chris Rock had to jab Hart about it when he came on the show. 

Kelly Clarkson’s On-Stage Mishap

“On-stage mishap” is putting it pretty mildly in this case. When the former The Voice coach appeared on Hart’s show, the conversation somehow turned to getting sick on stage, something they’ve both suffered, it turns out. Kelly Clarkson was poised to tell a story about a time when she had to walk off stage and “use” a trash can after eating something that didn’t agree with her before a show. 

Not to be outdone, Hart told a story about a standup show in Norway he did in which his “illness” hit him while on stage in the last seven minutes of his set. While it was not exactly the highlight of his career, he seemed to take an odd pride in Kelly’s moment being an “almost” accident on stage and his being a full-blown accident on stage. 

Pete Davidson’s SNL Audition 

The Bupkis star isn’t shy about letting the public in on his life’s story — I mean, it’s the whole plot of his Peacock original series. Still, it’s fun to hear him talk about milestones in his life in Pete Davidson's own words. That’s why Hart didn’t pass up the opportunity to ask him how, at just 19 years old, he managed to land a coveted spot on Saturday Night Live. It turns out, he has a few people to thank. 

While doing standup on the New York scene, he met Amy Schumer, who introduced him to Bill Hader on the set of the 2015 movie Trainwreck. After that, the man who went on to create the Emmy-winning series Barry recommended him for the show and got him an audition. Speaking to Hart, Davidson revealed how that audition went, what happened to him once he got to SNL and where he’s at in his life with fame and dealing with his imposter syndrome right now.

Tracee Ellis Ross’ Embarrassing Christmas

The actress and Hart had a long conversation about the Black creators and comedians who inspired them when they were young. Ross learned quickly that she had an affinity for doing comedic characters, which sometimes puzzled her family. When she was young and trying to break into the industry, she was a little strapped for cash around the holidays and had to think of a budget way to get Christmas gifts for everyone in her life. 

So, she did what she does best, wacky characters. She made a lengthy video in which she put all of her characters on display and sent them out to people in the form of 52 VHS tapes. When her famous mother, Diana Ross, got wind of it, she was less than thrilled. 

Jimmy Kimmel’s Long-Running Joke

Anyone who has ever watched Jimmy Kimmel’s show knows he likes to sign off by pretending famous A-List actor Matt Damon got bumped for time. It turns out, he credits that bit and a song about the actor gave his show a push in the right direction.

He told Hart that the joke and song going viral suddenly made A-List actors want to come on his late-night show for an interview, whereas before they were struggling with the “bottom of the barrel” for guests. He even dished a little bit on what it was like to be the host of a flailing show before the Matt Damon thing put his name on the map (without naming names, of course). 

Tune into Hart to Heart Season 3 on Peacock starting July 6. And watch both Seasons 1 and 2 now!

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