Amagansett, New York seems to be one of the least likely places for a Jelly Roll concert. The seaside enclave at the eastern end of Long Island, which is essentially part of the Hamptons, has long been the flexy summer retreat for Manhattan’s ultra-moneyed elite. It’s a place for the wealthy to enjoy extravagant luxuries. 

And while Jelly Roll’s concert there was played for a specially invited audience of SiriusXM subscribers and superstars like Bradley Cooper, Jon Hamm, Jimmy Fallon, Shawn Levy, George Stephanopoulos, Fox 5 co-host Rosanna Scotto, and a Real Housewife or two in attendance, there was a distinctly handmade, lo-fi warmth to this deeply gracious and galvanizing artist’s performance. 

In many ways, this speaks not only to his raucous fusion of country, rock, and hip-hop but also to his one-in-a-million ability to connect with people across all walks of life. One longtime associate noted that this was probably the oldest and wealthiest audience Jelly had ever played to, and he had them in the palm of his tattooed hand from the jump.

While the venue — Stephen Talkhouse, an approximately 200-person capacity club — may have led one to envision a small and intimate show, the event was held not inside the venue but in the back, under a sprawling, elaborately tricked-out tent that had several well-stocked bars. It was also festooned with plants and hay bales, which meant that the superstar audience who had been enjoying the open bar was watching Jelly while smelling hay. The event concluded with not just a meet-and-greet with the man himself but a free barbeque for all involved. As a result, the overall feel was much less prestigious as a limited-access concert, and much more of a giant party that cut through class divisions with infectious joy.

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The show was broadcast live over the network’s Highway channel and throughout the set. Jelly shouted out to listeners and thanked the SiriusXM team for its support and the role it has played in launching his late-blooming career. 

At nearly 40 years old, Jelly Roll has been at it for two decades, and now that his moment is here, he is clearly savoring it. He thanked the audience graciously multiple times, as well as his wife and two children, his mother and four siblings, his band, crew, and team. He also spoke at length about how far he’s come from the East Nashville projects where he was raised, not to mention the substance abuse and years in prison that he’s risen so far above, yet will always remain with him.

Like many special SiriusXM shows, Jelly Roll played a custom set, combining his hits and songs from his forthcoming album with fascinatingly curated covers that define his musical DNA.

He spoke of “smelling a skunk in the house” when he was a child and finally realizing it was coming from his older brother’s room, “and I heard this sound coming from behind the door.” The keyboardist then launched into the hook from N.W.A’s “Straight Outta Compton” and he played a medley of that song, Eminem’s “Lose Yourself” and Outkast’s “Ms. Jackson.” 

Jelly also spoke of his sister’s wide-ranging taste in rock music, which spanned from Nirvana and the Rolling Stones to the Eagles, and played both Green Day’s “Good Riddance” and a soulful version of Hootie and the Blowfish’s 1994 hit “Let Her Cry.” He talked about his mother and grandmother’s deep love of country, everything from George Strait and Alan Jackson to Waylon and Hank, and played both Garth Brooks’ “Friends in Low Places.”

It was and is the combination of all of these varying influences that makes up the core of who Jelly Roll is and has been as an artist, and with this event, he also showed the exciting and ambitious musical future still ahead of him.