Former Tommy Boy Records A&R executive Dante Ross was a shy, skinny white kid when he made the move from San Francisco to the Big Apple with his parents, who were desperately trying to save their marriage. After a series of run-ins with the local hoodlums who ran the pre-gentrification Lower East Side, he was forced to toughen up. While Ross managed to survive to see another day, his parents’ marriage did not.

As tumultuous as it was, however, his time in the LES exposed the young Ross to a multitude of cultures, which ultimately shaped his future. Anchored by the music of Bad Brains, Minor Threat, The Fall, Grandmaster Flash & the Furious Five, Bauhaus, Hüsker Dü, Jimmy Spicer, Soulsonic Force, The Clash and the Treacherous Three, Ross found his people, and a career in music would (serendipitously) follow.

Thanks to his friendship with Adam Horowitz, Adam Yauch and Michael Diamond—better known as the Beastie Boys—Ross landed a job at Def Jam Recordings, where he soaked up as much knowledge about the music business as he could.

At 22, he became an A&R rep at Tommy Boy. He’d go on to oversee the careers of De La Soul, Queen Latifah and Digital Underground. Later, after moving to Elektra Records, he signed Brand Nubian, Grand Puba, Del the Funky Homosapien, Pete Rock & CL Smooth, KMD (featuring the late MF DOOM), Leaders of the New School, Busta Rhymes and Ol' Dirty Bastard.

In his first book, Son of the City, Ross walks the reader down his path from New York City thug to A&R player extraordinaire—and the pitfalls he encountered along the way. Following is an excerpt from the memoir detailing the first time Ross heard De La Soul.

One night out on the town, I bumped into Monica Lynch, who ran Tommy Boy Records along with co-owner Tom Silverman. She mentioned to me that they were looking for an A&R person who would be responsible for talent scouting and overseeing the artistic development of recording artists. I immediately threw my hat in the ring. Monica had fire-red hair, green eyes and a beautiful smile. Originally from Chicago, she spoke in a Midwestern accent mixed with N.Y. hip-hop slang. She lived near the rundown Tommy Boy offices on First Avenue, in the same building Stretch Armstrong did many years later, coincidentally. Monica set up the interview, and it seemed to go well. She told me she had asked Daddy-O from Stetsasonic, a Tommy Boy act, about me and that he’d backed me up, as did a few others.

(L-r): DJ Clark Kent, Ricky Powell, Ross and Bobbito

She set a follow-up with me shortly after the Christmas holiday in January 1988, and we chopped it up for a little while. At the end of this meeting, she played me a cassette tape by a group that would change my life. As I heard the magical sounds waft out of her boombox, I was entranced. It was the weirdest, coolest thing I had ever heard. She asked me what I thought.

“That’s the best shit ever,” I said.

“Glad you liked it,” she responded.

“I love it,” I said. “It reminds me of Ultramagnetic crossed with Slick Rick. It’s so dusted.”

She laughed. “The group is called De La Soul and the song is ‘Plug Tunin’.’ They’re produced by Prince Paul from Stetsasonic. You know them?”

I told her what I knew of Paul and Stetsasonic but admitted I hadn’t heard of this group.

“Tommy Boy is going to sign them,” she said. “You’ll probably be their A&R guy.”

“Wait,” I said. “I got the job?”

I started working at Tommy Boy two weeks later, and I dove right into working with the De La crew. I clicked with them right from the get-go. We were almost the same age and had similar tastes in music and clothes. I was impressed by how unbelievably talented Prince Paul was.

De La Soul hailed from Amityville, Long Island. The three highly creative kids linked via music class. Prince Paul connected with Maseo via DJing and became their big bro and producer. His bandmate, Daddy-O, had brought the demo of De La to Monica Lynch for Prince Paul originally. There were several labels vying for the group, but Tommy Boy eventually inked the band. When I first met them, I was confused. They were three Black guys from way out in Long Island, which might as well have been another planet to me back then. But they dressed way out, even by my downtown standards. They rocked paisley shirts and Africa medallions.

Maseo was a big kid, broad-chested with a booming voice. He was the hooligan of the crew, and we bonded instantly. Posdnuos was a tall, dark-skinned brother with a flat top and a cool, colorful shirt, glasses and a wry sense of humor. Dove aka Dave was the quiet one, contemplative in a sense, seemingly very poised. They were progressive cats, and we clicked right away.

After meeting with them, I took them to the underground club Milky Way, which was located at the legendary Irving Plaza, which would later be the site of their first show. The night is kind of blurry, but I remember getting drunk and me and Maseo almost putting our hands on some kids, which was, I’m guessing, my fault. We made a little scene of sorts, and this sealed our bond. In the early days, I doubled as their road manager and booking agent. Basically, I was trying to supplement my Tommy Boy income.

Clockwise from top middle: Dan The Automator (in pink), an unidentified SXSW attendee,
Maseo, Trugoy The Dove, Del The Funky Homosapien, Posdnuos and Ross

I took them to L.A. for their first West Coast shows, which was also their first time in L.A. ever. During this trip, Pos and I almost got arrested for jaywalking on Hollywood Boulevard prior to us playing a show at [skating rink] World on Wheels. We were literally jaywalking in front of a cop car, paying it no mind, when we hear over the car’s megaphone: “You, the white guy with the stripped shirt, and the Black guy, get against the wall.” We kept walking. Initially, we didn’t know they meant us—until they made it very clear. They then berated us and only let us go after we explained we were from New York and didn’t know the jaywalking rules in L.A.

We also stopped by the legendary all-rap radio station KDAY and met then the most important program director and DJ in L.A., Greg Mack. This same gig is where we first saw what real live Crips and gangbangers looked like. I clearly remember seeing Crip-walking that night for the first time, as well as cats in Dallas Cowboys and Georgetown Hoyas gear throwing up Crip signs. I also met DJ Muggs (then of 7A3; later he would produce Cypress Hill and House of Pain), Ice-T and a very young Everlast, who was with us when we witnessed a huge gang-related fight break out at the venue that led to us being locked in the club while gunshots were going off outside. That night, we got an upfront view of the emerging L.A. rap scene.

Later, we bumped into the Beasties at an after-hours club in Hollywood. We concluded our trip with a BBQ at DJ Muggs’ pad the next day, where we ended up meeting a pre-Cypress Hill B-Real and Young MC, who was made to leave the party under duress by Mellow Man Ace and his brother, future Cypress Hill member Sen Dog. Why? I don’t know. But if Sen Dog was barking at me and I was Young MC, I would have left, too.