Drake Milligan

Sunday, June 21, 2026
Doors
7pm
Show
All tables have been booked for this event - for any inquiries, or to be added to the waitlist, click here
Drake Milligan

A student of classic Country music with the swagger of early Rock ‘n’ Roll, Drake Milligan is an electrifying entertainer who cites George Strait and Elvis Presley – the King of Country and the King of Rock ‘n’ Roll – as musical heroes, and his unique twist of traditional Country has been embraced by fans, peers, and major media including Billboard, PEOPLE, American Songwriter, USA Today, Access Hollywood, and more. In 2022, Milligan burst onto the national music stage with his debut album Dallas/Fort Worth, which topped the iTunes Country and All-Genre charts, landed him at #5 on Billboard’s Emerging Artists Chart, and was later named one of Billboard’s “Best Country Albums of 2022.” The Fort Worth, TX native has since performed on The Kelly Clarkson Show, The Grand Ole Opry, Stagecoach and CMA Music Festival, and recently became the first artist to perform on an F1 racetrack for the inaugural F1 Grid Gigs in Austin, TX.   Following his breakout debut, Milligan earned a #1 Canadian Country Radio hit with “Honky Tonkin’ About” (with The Reklaws) and carried that momentum into 2024 with his critically acclaimed EP Jukebox Songs, featuring fan favorite “I Got A Problem.” He also returned to primetime television for America’s Got Talent: Fantasy League before joining Cody Johnson, Lainey Wilson, Luke Bryan, and Blake Shelton on tour. With more than 230 million streams worldwide, Milligan is entering his next chapter with the release of his sophomore album Tumbleweed. The title track has already climbed into the UK Country Radio Top 10 as he kicks off his global “Tumbleweed World Tour,” continuing through 2026.

All events are 19+/No minors unless otherwise noted. Any ticket holder unable to present valid (Government Issued) identification indicating that they are at least 19 years of age will not be admitted and will not be eligible for a refund.

Hollywood Theatre is an entirely cashless venue, and only major credit cards, debit cards, and mobile forms of payment will be accepted at all events. Select points of sale at artist merchandise may still accept cash.

By entering Hollywood Theatre, guests consent to being photographed, filmed, or recorded as part of the general audience for promotional, marketing, and archival use across print, digital, and social media. Guests who do not wish to be photographed or filmed should speak with a staff member upon arrival or email us at info@hollwoodtheatre.ca

Please visit our website for additional terms & information. FAQ’s
This is an All Ages event. Two pieces of ID required for bar service, and may be requested for ticket authentication.

Hollywood Theatre is an entirely cashless venue, and only major credit cards, debit cards, and mobile forms of payment will be accepted at all events. Select points of sale at artist merchandise may still accept cash.

By entering Hollywood Theatre, guests consent to being photographed, filmed, or recorded as part of the general audience for promotional, marketing, and archival use across print, digital, and social media. Guests who do not wish to be photographed or filmed should speak with a staff member upon arrival or email us at info@hollwoodtheatre.ca

Please visit our website for additional terms & information. FAQ’s

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