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Brad Pitt, LeBron James or Jason Kelce: Rapper Lil Dicky Navigates His “Coolest Moments” Ever on New Heights Podcast

Utsav Khanna

Brad Pitt, LeBron James or Jason Kelce: Rapper Lil Dicky Navigates His "Coolest Moments" Ever on New Heights Podcast

It is one thing to live a cool life, a luxurious life, and a completely different one to party with Joel Embiid in a Philadelphia nightclub with one arm around his shoulders. Lil Dicky, as it happens, has experienced the latter.

On top of that, Lil Dicky has been a lifelong Philadelphia Eagles fan. Thus, it was “really cool” when he got an administrative email, signed by Connor Barwin, for a collaboration on the Eagles’ Christmas album. And there was no way he was letting that opportunity go. But meeting and basically befriending Jason Kelce; wasn’t enough to make the Eagles star the coolest person Lil Dicky ever met. And it isn’t a shade on Jason. The Philly legend continues to be a pillar for the community.

However, when you see the list of mega-stars that Lil Dicky, a.k.a. Dave, has had the fortune of working with, you’ll understand why he claimed what he claimed.

During his visit to the New Heights podcast, Lil Dicky was posed with many questions about the experiences he had in the entertainment industry. And most of these experiences, the comedically gifted rapper finds “the coolest moments” in his life. Even meeting his present company is something the rapper does not take lightly.

He first calls meeting Brad Pitt the “coolest experience of my life. nothing’s cooler.” But then he goes on to explain himself to the two extremely popular and talented celebrities he’s sitting across from. The rapper cum TV show creator adds, “First off, I love both of you guys, even though we’ve only known each other for 5 minutes, (but) Brad Pitt was definitely the coolest guy I’ve ever met.”

To which both Jason and Kelce unanimously responded, “I take zero offense to that.” Travis reiterates, “Zero. Zero,” while the brother duo struggle to stop laughing at how he has just compared them to Brad Pitt, one of the most famous actors in the world.

Later in the pod, Dave also talked about LeBron James giving him a shoutout on Twitter and forming a relationship with the NBA star over DMs, where they have apparently motivated each other over the years. At that point, the rapper acknowledged that he had used the phrase “coolest experience of my life” more than once, maybe even more than that.

Yet, he stood firm that his life and the show he has created have brought multiple experiences where he looks back and thinks, how did one get to do that? Whether it is directing Brad Pitt in a hostage situation or getting Don Cheadle to fart during the Met Gala, he seems to understand comedy at a very core level, and the writing in his show reflects the same. And even during his appearance on the podcast, he did not fail to lighten up the room.

Lil Dicky on the New Heights Show Was a Laugh Riot 

The New Heights podcast with Lil Dicky is one filled with laughter throughout, where the rapper continues to take some comedic turns during his elaborate account of the vast experiences his TV show has brought into his life. He even went on to quip that the character he portrayed in the hit show is much more successful than he is in his real life. Calling it a “bummer,” he does hint at a strong reason why he chose to take a long hiatus from creating the autobiographical show. Maybe he wants to create more music, music worthy of the character, “Dave.”

Yet, his appearance on the podcast was extremely eventful and the two brothers almost never stopped laughing throughout. Moreover, Lil Dicky was insightful throughout, with his fast wit and poetic timing. And Jason, Travis, and all the 92%ers would love to see more such appearances on the popular podcast.

About the author

Utsav Khanna

Utsav Khanna


Utsav Khanna, an NFL journalist with a keen eye for the game, has been covering the sport for the past two years, trying to bring the most interesting stories from and around the game. Armed with a degree in English Journalism from the prestigious Indian Institute of Mass Communication, he transitioned from a background in Public Relations to pursue his passion for sports reporting. Having penned over 200 insightful articles, he tries to bring in all the perspectives while writing as the NFL probably as one of the most intricate ecosystems in all of sports. A fan of the Pittsburgh Steelers, he admires the way Coach Mike Tomlin makes players buy-in into a system and entrusts them in challenging situations.

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