I’ll never forget Ricky Martin’s game-changing performance at the 1999 Grammy Awards.

I was with friends at a neighborhood bar only half-watching the ceremony. But when Martin took the stage, everyone stopped, stared and dropped their jaws. By the end of his song, “La Copa de la Vida”/”The Cup of Life,” the entire bar had fallen under his televised thrall. It was like a fully formed superstar had emerged out of nowhere and was ready to conquer the world.

Of course, by 1999, Martin had already conquered most of the world. His Grammy number and 1995’s “Maria” were massive hits just about everywhere but the United States. His utterly captivating and obvious charisma and talent not only won over the States but helped usher in a Latin pop boom that brought the likes of Shakira, Marc Anthony, Jennifer Lopez and Enrique Iglesias to the masses. (Christina Aguilera even tried to horn in on the boom and released an album in Spanish, even though she didn’t speak the language and had to sing the songs phonetically.)

Martin played Target Center on the tour that followed the Grammys but somehow has never been back to the Twin Cities until Friday, when he opened the Trilogy Tour with Pitbull and Iglesias. And he opened only in the sense he went first. The three performers swap spots each night, and Friday each played a headliner-style set, just at a truncated one-hour running time.

As such, all three guys made the most of their 60 minutes and played tight sets with little filler. OK, actually, Pitbull had some filler and Iglesias got a bit snoozy, but still.

If you’ve ever watched Martin interviewed on camera, particularly in the time since he publicly came out in 2010, he comes across as thoughtful, vulnerable and almost fragile at times. But his performance Friday instantly brought me back to 1999, gawking in awe at a guy who had the entire arena in the palm of his hand. And it was clear there were plenty of folks in the crowd there mostly for him, as he had the place singing and dancing from the first song.

Martin’s dozen song set included “Livin’ la Vida Loca” and his other early English language hits “Shake Your Bon-Bon” and “She Bangs.” But, like his overall career, songs in Spanish dominated, including “Lola, Lola,” “La Mordidita” and “Pegate.” And, beyond the power ballad “Vuelve,” peppy beats dominated, giving Martin plenty of opportunities to grin and wiggle around the stage, both on his own and with his athletic backup dancers.

A frequent visitor over the past decade, Pitbull has played the X, Target Center, the now-defunct Twin Cities Summer Jam, the Minnesota State Fair Grandstand and the amphitheater at Mystic Lake Casino. As he has in the past, Pitbull played the supreme party master ready to pump up the crowd in his tight trousers and mirrored aviators.

A Miami native born to Cuban immigrant parents, Pitbull began his career as a tough rapper type but found his success after softening his image and adding pop elements. His set was a trimmed-down take on his 2022 Grandstand show, but somehow still found time for a DJ set amid a show full of bangers like “Don’t Stop the Party,” “Hey Baby (Drop It to the Floor),” “Hotel Room Service,” “Time of Our Lives” and “Give Me Everything.”

Iglesias wrapped the evening with the most sedate set of the night. He’s not a particularly gifted vocalist and has long since leaned into his good looks to hold the audience’s attention. (It’s getting a bit harder since he began wearing a baseball cap full time.)

His upbeat numbers “Tonight (I’m Lovn’ You),” “Bailamos” and “I Like It” delivered giddy fun, but his other mid-tempo songs and ballads suffered from a sense of sameness. Indeed, I noticed the crowd had thinned somewhat during his set, which suggests to me that Ricky Martin would surely clean up if he returned for a full show.

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