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Why Simon Called Howie a “Bad Mentor” After Drake Milligan’s Swoon-Worthy Audition
With bragging rights on the line, Cowell didn't hold back when it came to Mandel's mentoring.
Rising country star Drake Milligan has celebrated number one hits — and charmed ladies around the globe — after debuting his original song, “Sounds Like Something I’d Do,” on America's Got Talent Season 17. So when it came time for the judges to choose their Dream Teams for America's Got Talent: Fantasy League, Howie Mandel scooped up the talented Texas native whom he described as “one of the most successful Acts in AGT history.”
The singer-songwriter had a banner year that cemented his place in the country landscape and wanted to switch things up for Fantasy League, which Simon Cowell thought was a bad call.
For the first time, the “New Elvis of Country” performed a song that he had not penned himself: “I want to show that I’m not just a one-trick pony,” he told Howie in a Fantasy League interview, adding, “I believe in this song.”
Both agreed the change would be scary, but Mandel encouraged the young artist to take a risk.
"This is a big swing, but you can’t hit a homerun without taking a big swing,” the Mentor said.
What song did Drake Milligan sing on AGT: Fantasy League?
Drake chose “Don’t Leave Me Loving You” from his forthcoming EP “Jukebox Songs,” which is set to debut on February 16. It was written by country artists Bobby Pinson, Matt Rogers, and Grammy-winner Ben Stennis. The melodic heartbreak ballad was a departure for Drake — known for his energetic country twang — but showed off his smooth baritone voice. Cowell, however, wasn’t quite feeling it.
Thinking this was a Drake original, Cowell said, “I love Drake as an artist and also as a person… however, that wasn’t my favorite song you’ve ever done.”
When Mandel revealed the song wasn’t written by Drake, Cowell double-downed: “This is bad mentoring. You are a great writer, and I didn’t feel there was a connection with you and that song.”
What happened to Drake Milligan on AGT?
Make no mistake — Drake has blazed a trail of success on AGT, bringing down the house with his lively original songs like “Kiss Goodbye All Night.” After cruising into the finale, Drake finished in third place overall, narrowly missing out on the grand prize.
When the crooner returned to America’s Got Talent in September 2023 to debut his current single, “I Got A Problem,” he got a standing ovation. Simon enthused, “Amazing, Amazing, Amazing!” before inviting him in front of the world to join the Fantasy League.
What is Drake Milligan doing now?
The country singer has come a long way from his days as a young Elvis impersonator. After his time on the AGT stage, Drake released his debut album, “Dallas/Fort Worth,” which was named one of the best country albums of 2022 by Billboard. Many accolades, award nominations, and a cross-country tour followed.
Aside from the new album coming out in February, Drake has a lot in store for this year. He’s kicking off an international tour in February, joining country superstar Cody Johnson for 10 arena dates. He’ll also travel across the pond, performing hits like “Goin’ Down Swingin’” in Europe, the U.K., and Australia.
Of course, he’ll showcase his new songs as well, which he describes on his official website as “a continuation of the old-meets-new Country sound I’ve always gone for, and this time with my friend Trent Willmon at the reins as producer, I’m very excited to keep this honky tonk train rollin.’”
All aboard that honky tonk train!