On June 14, 2024, Jeremy Tepper, who served as Sirius XM Outlaw Country's program manager since its inception, died.

[2] Current show hosts include: Former hosts include: The Outlaw Country Cruise is an annual seven-day cruise aboard the Norwegian Pearl from Miami, Florida to Great Stirrup Cay, Bahamas and Cozumel, Mexico.

The cruise is attended by various artists and hosts heard on Outlaw Country.

The cruise's 2023 lineup included The Mavericks, John Anderson, Lucinda Williams, Steve Earle, Ray Wylie Hubbard, Old 97's, Kathleen Edwards, Carlene Carter, Elizabeth Cook, The Waco Brothers, Mike and the Moonpies, Jesse Dayton, The Supersuckers, Vandoliers, Bill Kirchen, Redd Volkaert, Dallas Wayne, Tommy McLain, C.C.

Adcock, Linda Gail Lewis, Joe Carrasco, Augie Meyers, Rosie Flores, Slim Jim Phantom, Warner E. Hodges, Sarah Borges, The Mastersons, Roger Alan Wade, Mary Lee's Corvette, Andrew Leahey, and Mojo Nixon.