When Eagles fans head to Madison Square Garden for the show tonight, they will get a little visit from the Boss. No, not Bruce Springsteen, but from Jim Dolan, the 59-year-old billionaire who booked his band to open for the classic rockers when they play the venue he owns.

The history of rock and roll is filled with stories of the downtrodden — the dockworkers that populate Bon Jovi songs, Springsteen’s hard luck cases and Mellencamp’s little ditties about American kids doing the best they can. The 1% has Dolan and his band, JD & The Straight Shot, to fill the void in the musical market and the iPods of the upper crust with bluesy tunes like “Governor’s Song” about the taxation rate and “Fall From Grace” about the schadenfreude of watching a governor felled by a scandal.

This month, Dolan, the president and chief executive of Cablevision and the owner of the New York Knicks and the New York Rangers, is living out his musical dream. His band will release their first album, Where I’ve Been, and to celebrate, he booked the band a gig —opening for the Eagles at the little venue he owns, Madison Square Garden. “I always said I wasn’t going to do it,” Dolan told the New York Times of playing the Garden for the first time, “but this record made me do it.”

While Dolan’s checking account may be larger than most musician's, he does share some of the concerns of the average street busker, especially when it comes to connecting with the audience: “I worry about the other ways that people know me. I worry that they aren’t going to listen to the music,” he told the New York Post. “Are they going to look at the music and go, ‘I don’t like how the Knicks are doing this year’?”

Dolan isn’t playing music just for fun or profit, though. “The artist in me needs to be free,” Dolan explained. The songs he writes may not be to everyone’s taste, but his artistic expression will not be hampered by shareholders’ musical interests. “I'm entitled to my opinion. I am not the chairman, CEO, etc., standing up there on that stage. I am the singer-songwriter,” he told the Post.

Years of battling it out with Knicks fans and government officials intent on keeping the Garden in midtown Manhattan, have not inured Dolan to the fear of criticism, though. “You are definitely putting it out there and making yourself vulnerable and susceptible to criticism, and since it’s so personal, you run the risk of being hurt,” he said to the Post.

Billionaire musicians are people, too.