Christopher Cross Financed his Debut Album by Selling Drugs

When Christopher Cross burst onto the music scene at the end of 1979 with his Grammy-winning self-titled debut album, he seemed like a banker or someone who’d be selling insurance door-to-door. He didn’t look anything like your average rock star.

He sounded even less like one. Although he was weaned on the sounds of ’70s classic-rock gods Steely Dan, his mellow, easy-listening 1980 No. 1 hit “Sailing” was like a breezy lullaby that eased audiences into a post-disco reverie.

But as Cross himself explains in the new filmYacht Rock: A Dockumentary, he was actually a lot more hardcore than he sounded or looked. In fact, his massive debut album might never have existed at all had it not been for his knack for selling drugs — and indulging in them, too.

“The original demos I did, all the songs ended up on the record,” Cross, 73, says in the documentary, which premiered Nov. 13 at the DOC NYC festival. “I financed my original songs by selling weed. I had a very successful weed business, and I bought a tape machine and some consoles and stuff and invested in a studio in Austin.”

He ended up sending his tape to the wrong person at Warner Bros. Records — an assistant who liked it so much that he went to lunch with Lenny Waronker, then head of the label’s A&R department, and forced him to listen to the tape in the car.

“Lenny told me years later that had I just sent it to A&R, it would have been rejected outright, because they weren’t really accepting anything. So it was pretty serendipitous that I sent it to the wrong guy,” Cross says.

He would have a short-lived but impactful career. His debut album sold five million copies, produced four hit singles (“Ride Like the Wind,” “Sailing,” “Never Be the Same” and “Say You’ll Be Mine”) and won five Grammys, including Album of the Year. His fifth single, 1981’s “Arthur’s Theme (Best That You Can Do),” would hit No. 1 and win an Oscar.

By the mid ’80s, Cross’ chart era was pretty much over, despite its auspicious start at the turn of the decade. Like his career, his debut album’s first single, “Ride Like the Wind,” which went all the way to No. 2 on Billboard‘s Hot 100 and became a yacht rock classic (with Doobie Brother and lifelong friend Michael McDonald on backing vocals), also had drug-fueled beginnings.

“I was playing at a club in Houston. We were doing ‘[Nineteen Hundred and Eighty Five]’ by [Paul] McCartney of Wings, and in the middle of that song, I started doing this [mimics the driving musical hook of ‘Ride Like the Wind’] and people would go crazy. They started dancing and moving around. It just seemed to really connect with the audience, so we would just jam on that riff.”

He continues: “So then we drove from Houston down to Austin to record, and I was sitting in the front seat of the van and had taken acid, and I wrote the words to ‘Ride Like the Wind,’ driving from Houston to Austin, on acid.”

Yacht Rock: A Dockumentary will debut Nov. 29 on HBO and be available to stream on Max, following its Nov. 13 premiere at the DOC NYC festival.