More than a decade ago, Don Omar and Daddy Yankee were collaborators on underground hits like “Gata Gangster,” but their relationship turned sour. Some say it was over publishing rights, others contend it was due to feuding financial backers; no one will speak on the record. But whatever the reason, Omar (real name: William Landron) and Yankee (real name: Raymond Ayala), the rising stars of the then-new reggaeton movement brewing on the streets of Puerto Rico, let their differences devolve into the most fiery rap battle in Latin music history (sample lyric, from Yankee: “Everyone knows there’s no one more plastic than Landron”).
But in 2009, the two shocked audiences by appearing onstage together in Puerto Rico, and again at the red carpet at the Billboard Latin Music Awards. Immediately, big-money offers for a tour started pouring in, although nothing materialized.
Until now: “The Kingdom” — a 60-date Yankee/Omar tour that is scheduled to run for two years — will launch Dec. 5 in San Juan, Puerto Rico. The partnership also includes a joint album and a TV show for the two artists, who between them have 11 No. 1 hits on Billboard’s Latin Albums chart, 28 top 10 hits on Hot Latin Songs, over 50 million followers on Facebook and Twitter alone, and have sold more than 5 million albums in the United States, according to Nielsen Music.
“If this were the mainstream market, it’d be like putting together Rihanna and Beyonce,” says attorney Edwin Prado, who represents both artists.
But the question remains: Why now?
“I was motivated by doing something completely different — and by the size of the offer,” says Yankee, 38. “This is a sport, and I like to be the best athlete.” Omar has slightly stronger words. “Let me clarify: I am not his best friend, and he is not my best friend,” says the 37-year-old. “But we respect each other. That desire to be the best is what has pushed us to be better.”
The tour is framed as a musical boxing match, with the two artists trading off musical sets or “rounds,” and with fans voting for their winner in each city through an app designed for the event. “Two kings, one throne,” says veteran concert promoter Raphy Pina, who took over Omar’s touring in 2013 and came up with the concept. It was Pina, who has a long-standing relationship with both artists, who initiated conversations between them. Once he knew that both were interested in working together, getting the right concept was key.
“The relationship between the two of them was already good again. I had a good relationship with Yankee,” Pina explains. “And I understood people like concepts, and this was the biggest concept I could come up with. It hasn’t happened before, and it won’t happen again.”
Both Omar and Yankee say they welcome the competition. “There’s a professional rivalry, and we’re both going to show our best,” says Omar. “It’s stressful, and I love it.”
Things between Omar and Yankee have been moving along so well, that late last year, they recorded together for Don Omar’s album, The Last Don 2, released this past June.
That was the first step toward the actual contract, executed in June while Don Omar was in the studio in Puerto Rico and Yankee on the set of La Voz Kids in Orlando.
Don Omar signed first, and the copy that eventually made its way to Yankee’s hands came with a hand-written note from his long ago friend, then foe, now friend again:
“Thank you,” it said, “for giving me the opportunity to work with you.”
An edited version of this story originally appeared in the Aug. 22 issue of Billboard.