Shaboozey engaged thousands of attendees at Bridgestone Arena when he performed his viral single during the 58th CMA Awards on Wednesday night (November 20) in Nashville, Tennessee. His medley of “Highway” and “A Bar Song (Tipsy)” arrived after the trio of hosts — Luke Bryan, Peyton Manning and Lainey Wilson — raised red solo cups in honor of late country legend Toby Keith.

First-time nominee Shaboozey started his performance with one of his newest singles, “Highway,” which made its debut in September. The song followed the trailblazing artist’s “A Bar Song (Tipsy),” which reached several major milestones since the rapidly-rising star dropped it earlier this year.

Shaboozey recently laughed at some of his old posts on X, formerly Twitter, as he reflected on how far his career has gone in the last year. During an interview with Gayle King on CBS Mornings, Shaboozey reacted to his posts: “What I gotta do to blow up? To show y’all I really got this music thing on lock. Do I gotta go on a rant? Date a tik toker? Tell me… I appreciate all the people that do support me and are true fans. Hopefully we come back to this tweet next year and have a good laugh.”

Shaboozey, who will make his Saturday Night Live debut next month, told King he was “cracking up for sure.”

The star-studded lineup of performers at the CMA Awards also includes Chris Stapleton and Post Malone, Kelsea Ballerini with Noah Kahan, Brooks & Dunn with Jelly Roll, Eric Church, Luke Combs, Ella Langley with Riley Green, Cody Johnson, Megan Moroney, Kacey Musgraves, Bailey Zimmerman, Dierks Bentley (featuring Molly Tuttle, Sierra Hull and Bronwyn Keith-Hynes), Luke Bryan, Ashley McBryde, Thomas Rhett and Teddy Swims, and Lainey Wilson. Presenters include Simone Biles, Clint Black, Jeff Bridges, Mark Collie, Jordan Davis, Freddie Freeman, Don Johnson, Jackson Laux, Little Big Town, Dustin Lynch, Katharine McPhee, The Oak Ridge Boys, Taylor Frankie Paul, Carly Pearce, Caleb Pressley, Nate Smith, Daniel Sunjata, Mitchell Tenpenny and Billy Bob Thornton. The Country Music Association also revealed the all-star group of artists — Jamey Johnson, Miranda Lambert, Parker McCollum, Chris Stapleton and Lainey Wilson — paying tribute to country legend George Strait. Strait is the recipient of the 2024 Willie Nelson Lifetime Achievement Award.

Check back with iHeartRadio for a live-updated list of winners throughout the evening, a gallery of the most stunning red carpet looks, coverage of can’t-miss performances and more throughout the evening. The 58th CMA Awards is airing on ABC on Wednesday evening, and will be available next day on Hulu.

Medical Monday with Randy Bell presented by St. Dominic’s