Role Model, who is featured on PEOPLE's list of 100 Reasons to Love America this year, has made it a tradition to bring out a special guest to join him on stage while performing the song "Sally, When the Wine Runs Out." The singer brings out a celebrity guest for the special moment, and sometimes even a fan from the audience. In a recent interview with Rolling Stone, Role Model expressed his desire to have Kacey Musgraves join him on stage, saying "We're playing a few of the same festivals, so we'll see if we can make that happen."

Conan Gray as "Sally"

At the Gov Ball Music Festival in New York City, Conan Gray joined Role Model on stage as the day's "Sally." Gray gave the singer a big smooch before dropping to the ground and then hopped around in his "Wish I Were Sally" T-shirt, mouthing along to the words.

Reneé Rapp as "Sally"

In April, Reneé Rapp joined Role Model on stage with a huge smile on her face. With a beverage in one hand, Rapp jumped around while interacting with both the crowd and Role Model, who matched her energy perfectly.

Bowen Yang as "Sally"

When Role Model made his Tonight Show debut, he brought out Bowen Yang to join him on stage. The SNL star had the choreo down as he walked out on stage after hearing the magic words: "Where's my Sally tonight?"

Role Model's Mom, Susan Pillsbury, as "Sally"

In April, when Role Model brought his tour to Boston, he had an extra special lady join him as "Sally" His proud mom, Susan Pillsbury, danced around in her "New England born and raised" T-shirt after giving her son a hug.

Jake Shane as "Sally"

At the House of Blues Dallas, influencer and podcaster Jake Shane hit the stage to the sound of the crowd's cheers. Before leaving the stage, he blew the singer a kiss and gave him a hug before waving to the audience. This wasn't the first time the two entertainers had collaborated; Role Model appeared as a guest on Shane's Therapuss podcast on two separate occasions last year.

Dylan Minnette as "Sally"

In a look that made us double-take, Dylan Minnette walked out at an L.A. show earlier this year in a tight white long sleeve shirt ready to strut around the stage.

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