Actor and comedian Adam Sandler kicked off his You’re My Best Friend comedy tour in Florida over the Sept. 5–7 weekend, delivering a mix of comedy, music, and nostalgia for audiences.
Kevin James. Adam Sandler. Michaelangelo. Vanilla Ice.
— Phinstonedcards (@phinstonedcards) September 6, 2025
All on one stage! pic.twitter.com/Zn4ci4JwNN
At shows in Jacksonville, Tampa, and Miami, Sandler surprised fans by performing the 1990 hit “Ice Ice Baby.” He began by playing the song’s familiar opening chords before introducing rapper Vanilla Ice, who hyped up the crowd. “Everybody is officially a teenager right now,” the rapper said, encouraging the audience to relive the ’90s. Vanilla Ice is currently touring with the I Love the ’90s concert series.
Sandler was also joined on stage by longtime collaborator Kevin James, his Grown Ups and Paul Blart: Mall Cop co-star. At one point, James danced energetically alongside Vanilla Ice, accompanied by a performer dressed as Teenage Mutant Ninja Turtle Michelangelo — a nod to the rapper’s 1991 track “Ninja Rap.”
During the Miami performance, Sandler and James staged a comedic sketch in which James pretended to be an audience member upset about missing his friend. The bit ended with the two breaking into a lighthearted duet about their friendship, with Sandler joking about James’s off-key singing.
Sandler’s set also included a rendition of his emotional tribute to late comedian Chris Farley, his Saturday Night Live castmate and Grown Ups co-star, who died in 1997.
The North American tour will continue through the fall, with stops planned in New York City, Boston, Toronto, Chicago, and Seattle, before concluding in Las Vegas on Nov. 1.
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