The Home hitmaker collaborated with Will Ferrell's Funny Or Die production company to create the promo for his new single Drunk on a Plane, which features Bentley as a faux airline pilot leading a group of rowdy passengers downing booze during a flight.
Bentley reveals he actually wanted to recruit Helms for the clip, but the actor turned the offer down.
He tells Rolling Stone, "I texted him (Helms) asking if he'd do it, knowing full well that he's just too big of a star to be in a music video. He should have done it, the video's at number two."
To make up for the snub, the actor invited him to play at the annual Tennessee music festival on Sunday (15Jun14), when he hosted the Bluegrass Situation Superjam.
Bentley, who made his Bonnaroo debut in 2007, performed a pair of songs with Helms' band The Lonesome Trio, and artists including Sarah Jarosz, Lake Street Dive, and The Black Lillies were among the Superjam's line-up.