Jay Z and Phish have more in common than one might suspect. They both rose out of an underground scene to incredible prominence in the mid-1990s despite a lack of mainstream pop hits, and both attracted an enormous audience with their amazing live performances and complex, witty tunes. They have a history of announcing retirements with great fanfare, and then roaring back just a few years later with new projects. They're also not exactly strangers to the world of illegal drugs or the U.S. court system.
But the only time their worlds actually collided was one incredible night at Brooklyn's KeySpan Park on June 18th, 2004. Phish had just kicked off a much-hyped farewell tour and Jay Z was in "retirement" mode himself after the release of The Black Album the previous year and his retirement party show at Madison Square Garden. Three songs into Phish's second set, right after "Down With Disease," out walked Jay Z to stunned applause. "We're going to bring out a friend of ours," says Trey Anastasio. "Brooklyn's own. Great musician and great singer. Can you put it together for Jay Z."
"You guys having fun out there?" Jay Z asked the crowd. "Brooklyn make some noise!" He then launched into "99 Problems." As Kelefa Sanneh of the New York Times pointed out, the song really connected with the jam band audience. "Jay Z rhymed about eluding an illegal search ('Well, my glove compartment is locked, so is the trunk in the back/ And I know my rights, so you gon' need a warrant for that'), there was a sympathetic roar," he wrote. "Who says Phish fans and hip-hop stars have nothing in common?" They followed it up with "Big Pimpin'."
"They just reached out to me to do something," Jay Z told Rolling Stone days later. "I always believe in just good music and bad music, and I want to try new things. I saw this as a great opportunity. I went out and had a great time, and I've never performed in Brooklyn like that. That was beautiful … I just kept hearing their name and how strong they was live, how big a following they had live and that they've been doing it for like twenty-one years. That was amazing to me. I was intrigued."
Two months later Phish wrapped up their farewell tour with the three-night Coventry festival, which turned into a mud-soaked disaster when rains ruined the grounds and many fans couldn't even get to the site. It would have been a lousy way to end things, but less than five years later they came back and have been touring heavily ever since. Sadly, Jay Z has yet to perform with them again.