Adam Levine Perfectly Impersonates Frank Sinatra in Jimmy Fallon’s Musical Challenge

The Voice Coach was the very first celebrity to spin the “Wheel of Musical Impressions” on The Tonight Show.

“Wheel of Musical Impressions” is one of the most popular recurring games in The Tonight Show Starring Jimmy Fallon history — and back in September 2014, Adam Levine was the very first player.

After explaining how the game worked, Jimmy Fallon invited The Voice Coach to spin the wheel first. Levine landed on Frank Sinatra singing “Head, Shoulders, Knees & Toes.” We all know the Maroon 5 frontman has “Moves Like Jagger,” but it turns out he also has a perfect impression of Ol’ Blue Eyes, which he flaunted as he crooned the children’s song.

After Fallon’s turn, tasked with covering “Rude” by MAGIC! while singing like Bob Dylan, Levine’s second number was the Sesame Street theme song, performed by Michael Jackson. Even after a delayed start, Levine thrilled Fallon and the audience with his impeccable impression of the King of Pop.

“I couldn’t find the key… that was rough, man,” said Levine after finishing his Jackson jam.

Watch Levine’s o.g. “Wheel of Musical Impressions” game below.

The Tonight Show Host followed with a “Fancy” version of “Old MacDonald Had a Farm,” in which he sang the nursery rhyme like Australian rapper Iggy Azalea. The final round belonged to Levine, who had to perform “The Muffin Man” as Eddie Vedder from Pearl Jam. Fallon couldn’t help but join in as they both wailed in their best ’90s grunge rock voices.

Levine’s segment instantly set the bar quite high for future challengers like Ariana Grande, Christina Aguilera, Jamie Foxx, and more. In April 2024, Levine returned to The Tonight Show to spin the wheel once again, channeling singers like Bruce Springsteen and Dave Matthews to sing more classic nursery rhymes.

Why Adam Levine is back on The Voice in Season 27

Levine left The Voice in 2019, but he recently returned to the red chair for Season 27, which premiered in February 2025.

“The only way to sum it up is that just energetically… the opportunity came at the right moment and I was really ready, and we started talking about it and one thing led to another and here I am. It was that simple,” he told NBC Insider earlier this year, on his decision to return. “It didn’t involve too much deliberation or overthinking. I kind of just felt ready. I was really happy to come back and experience it again with these three wonderful people.”