Over the last 44 years, Allen Grubman has built Grubman Shire Meiselas & Sacks from a small firm into an international legal powerhouse covering all areas of entertainment. Its core has always been music, the area where Grubman has established himself as a confidante of the industry’s biggest stars and moguls, a fierce negotiator and a dealmaker of the highest order—not to mention the most colorful attorney in the biz. His connections to labels, executives and artists are legendary—every CEO of a major music group has retained Grubman as a consultant over the last 40 years. What’s more, he represents or has represented eight of the other 17 industry figures profiled in this volume.

No other music-business attorney has cast as large a shadow or left a bigger footprint over the last 40 years than Grubman. He’s street-smart, funny and gregarious; powerful captains of industry enjoy his company. And he enjoys a big lifestyle.

Grubman entered the music business at a time of transition. His first job found him stepping into the old-school way of doing business—visiting people like Morris Levy to get a bill paid and walking out with a five-figure settlement—in green, inside a brown paper bag. He saw the adversarial side of the relationship between labels, managers and artists.

“You had to adapt as the times changed,” Grubman has said. “The artists have a difficult time understanding that the [executives] they have to meet are very different people than the ones they would have met 10 or 15 years ago. One of the functions a lawyer performs is, he becomes the bridge between the artist and the executives. If you’re able to do that, you’re able to succeed. I think I’ve done that.”

By the time he hung up his own shingle, in 1974 at the dawn of the disco era, he saw the advantage of firm negotiating, avoiding litigation and—in a move away from legal tradition—embracing practices that in other areas of the law could represent conflicts of interest. The music industry had grown up; legal battles were with corporations, not seat-of-the-pants operations. He saw value in deal-making and partnerships rather than going mano a mano over royalty rates.

He also pioneered the concept of not charging an hourly rate and instead handing a bill to a client after a financial settlement had been made. It quickly made him a millionaire—Forbes had him in the top five of corporate lawyers in the late ’70s based on individual earnings. Businessweek later called him “the most powerful lawyer in the music business.”

His career has rolled out like a superstar’s—one hit leading to another. Success with The Village People and Hall & Oates early on led to Billy Joel for 52nd Street, then Bruce Springsteen prior to his breakthrough Born in the U.S.A., and then John Mellencamp; each artist was impressed with the results of Grubman’s efforts to get larger advances and better royalty rates. U2, Madonna, Lady Gaga, Sting, Elton John, Lionel Richie, Sean Combs and others fill his high-end client roster, along with iHeartMedia, Spotify, Live Nation, Irving Azoff, Doug Morris, David Geffen and Jimmy Iovine. Interestingly, Grubman is no fan of rock & roll—he prefers the music of Frank Sinatra—and therefore has never said, “I listened to your record and I think it could be a hit.” But he has great instincts and can smell success from across the room.

“Anybody who knows me knows that when I represent a client in a transaction, I kill for that client—sometimes to the frustration and anger of the person on the other side of the table—whether or not that person also happens to be a client,” Grubman told the L.A. Times in 1997. “When the guy on the other side of the table sees me trying to get the absolute best deal for my client in that transaction, he realizes that I am going to kill the same way for them when I am hired to work on some future transaction on their behalf.”

In the mid-1990s, Grubman found himself in two of his more famous battles. In 1995, Time Warner’s Michael Fuchs refused to compromise with Interscope founders Ted Field and Jimmy Iovine on the release of several rap albums.

According to Field, interviewed in the L.A. Times, Grubman told Fuchs, “I represent 48 of the top 50 people in the record business. You don’t renege on a deal. You don’t do business that way. This is too small a business to act that way.’ And that was that—we got out.”

Check out the entire Grubman profile here.