Adam Sandlerkicked off his You’re My Best Friend Tour this weekend in Jacksonville, Florida. For fans who have waited years, even decades, to see The Wedding Singer actor live, Saturday’s tour opener did not disappoint. Sandler even surprised fans with guest appearances by two ‘90s icons Sandler happens to call close friends.
Fans left feeling like “old friends” watching Sandler strum his guitar and entertain the crowd with his brand of musical comedy, bathroom jokes and all. But what made the tour’s kickoff show so special were Sandler’s special guests, Vanilla Ice and Grown Ups co-star Kevin James.
Wearing his signature hoodie and sunglasses, Sandler vibed on the guitar as he strummed the iconic bassline to “Ice Ice Baby” before bringing to the stage Vanilla Ice (whose real name is Robert Van Winkle) himself. Paul Blart: Mall Cop star Kevin James joined the pair on stage, dancing and mugging for the audience. The trio was also joined by Michelangelo from the Teenage Mutant Ninja Turtles, just because.
One stunned fan commented the Adam Sandler/Kevin James/Vanilla Ice mashup was “not on my 2025 bingo card.”
The performance was peak ‘90s (and by the way, Vanilla Ice sounds terrific), and fans couldn’t get enough of the ‘90s throwbacks, all on one stage.
Related: Adam Sandler Makes Hilarious Tribute to Favorite NFL Star: ‘Sorry for the Disgusting Face’
Adam Sandler Brings Out ‘90s Comedians to Open the Tour
Vanilla Ice and Kevin James weren’t the only ‘90s stars to grace the stage to open Sandler’s You’re My Best Friend Tour in Jacksonville.
• Producer and comedian Joseph Vecsey opened the show
• SNL alum Rob Schneider followed with a comedy set
• Fellow former SNL alum Kevin Nealon followed with a spot-on comedy set
With the crowd warmed up and ready, Sandler took the stage. He ditched his regular basketball shorts in favor of khakis, a hoodie, and sunglasses, and entertained the crowd with a combination of new and old songs, jokes, and bits – some of which were entirely blushworthy, but hilarious.
Adam Sandler Pays Tribute to Chris Farley
It wouldn’t be the You’re My Best Friend Tour without Sandler paying homage to his best friends. In addition to the hilarious crew of friends who joined him on stage, the Happy Gilmore 2 star closed the show with a tribute to former SNL co-star Chris Farley, who died in 1997.
Sandler even brought the audience to tears with his final number, a reworked version of “Grow Old With You” from The Wedding Singer, rewritten for his wife of 22 years,Jackie Sandler.
Sandler knows how to get the laughs and the tears, while making everybody in the audience go home feeling like they’re his best friend, too.
Related: ’90s Sitcom Star, 60, Looks ‘Hot’ During Surprise Jelly Roll Performance
This story was originally reported by Parade on Sep 7, 2025, where it first appeared in the News section. Add Parade as a Preferred Source by clicking here.
‘ The preceding article may include information circulated by third parties ’
‘ Some details of this article were extracted from the following source www.yahoo.com ’
