Brad Klein is standing in the glass doorway at World Street Kitchen in south Minneapolis, on his cellphone, smoothing things over.

The 52-year-old Minneapolis native is used to doing that — he’s a real estate agent. But this is different: On the other end of the call is Jamaican music legend Millicent Todd, aka Patsy — one of the headliners of the Klein-assembled Cariba Days: A Tropical Movie and Music Fest, happening May 13-15 at Pepito’s Parkway Theater in south Minneapolis.

Patsy, who lives in Florida, is under the impression that the show was taking place in Jamaica — she couldn’t locate her passport. “Don’t worry,” Klein tells her. “You don’t need a passport to come from Florida to Minneapolis.”

Klein made his own passport from Minneapolis to Jamaica: His documentary, “Legends of Ska,” is Cariba Days’ centerpiece. Patsy is one of a smorgasbord of talking heads historicizing the music, which enjoyed its mid-1960s heyday in the wake of Jamaica’s independence from England. Ska would fall out of favor — first to the slower rock steady, then, by the late ’60s, to reggae.

“I wanted to show the world that there’s a lot more to Jamaican music than Bob Marley, Jimmy Cliff and Peter Tosh,” Klein said. “So much music comes from it. Rap came from the sound system guys: U-Roy in Kingston, chanting over rhythms. That’s where it started.”

“Legends of Ska” is accompanied at Cariba Days by six other films, a handful of bands — including original ska musician Phil Chen and local ska band the Prizefighters — and Klein himself, spinning records as Steady Rock Sound. He’s bringing in his own sound system for the occasion; he’s also supplying “a big vat of Walkerswood, my favorite jerk seasoning,” with which Pepito’s cooks will “jerk” their Mexican menu. “Whatever’s on the menu, you can jerk it — enchiladas, anything,” he said.

The Parkway has shown Klein’s documentary a few times since its release last year. It’s drawn well enough that owner Joe Senkyr Minjares suggested Klein schedule a full weekend; Klein went for a full-on fest, getting quick “yes” replies from a half-dozen directors he’d met on the festival circuit. (It helped that Klein offered the filmmakers small fees — most film festivals don’t.)

Most of the films, a mix of docs and dramas, are recent, aside from “18 on Steel,” a well-regarded Trinidadian short from 1964 about the Steel Band Jamboree held at the U.S. Naval Base in Chaguaranas, and the 2004 documentary “Calypso Dreams,” about the roots of Trinidad and Tobago’s pop style.

Legendary encounter

“Legends of Ska” was a decade and a half in the making, but Klein has been obsessive about Jamaican music for decades. After college in upstate New York, Klein landed at the D.C. reggae label RAS Records in the late 1980s. “I got my dream job right out the gate,” he said. He became an aerobics teacher in San Diego in the early ’90s (naturally, he taught “reggaerobics”) and returned to Minneapolis in 1995, where for a decade he has been a real estate agent.

Klein’s Radio K ska show got the ball rolling, giving him an “in” to interview artists such as Derrick Morgan, ska’s first “king,” who in 1960 held each of Jamaica’s top seven chart positions. In 2000, after the Buena Vista Social Club phenomenon, Klein decided to try a similar tack with ska, reuniting a number of the original musicians and players for a concert in Toronto in 2002.

“It was like ska camp — the reunion they never had,” Klein said. “Some of them hadn’t seen each other in 30, 40 years.”

Among the headliners were Morgan and Patsy, who’d had a duet smash with “Housewives’ Choice.” “No one thought I was going to get Patsy,” Klein said. “I left her dozens of messages. She never returned the calls. I called on the 4th of July; the [event] was on the 12th. Last try, and Patsy picked up the phone.”

She told Klein: “I’ve got a good feeling about this.”

Rare footage

For Cariba Days, Patsy reunites with another duet partner, Stranger Cole. Klein contacted him via the Prizefighters, who’d backed up Cole in Chicago a few years back. When Klein asked Patsy if she was willing, she responded, “OK, honey, I’ll do it.”

The Toronto show provided much of the interview footage that forms the backbone of “Legends of Ska.” Klein’s timing was pivotal: “I brought 30 people up to Toronto for that show,” he said. “Half of them are gone now.”

At a London screening last year, Rico Rodriguez, the legendary ska trombonist who later played with first-wave British ska band the Specials, took a curtain call; he passed away two months later.

Klein had figured his performance footage would be enough to secure financing for the rest of the film. Nope. “It’s really crazy how hard it is,” he said. “It all comes back to raising the money. The producer does 95 percent of everything, and 95 percent of that is raising the money. I’m still trying to raise finishing funds. But I made the movie that I wanted to make.”

“Legends of Ska” recently won best documentary at the Jamaican Film Festival (“the deck was stacked in my favor, but you take ’em where you can get ’em,” Klein said with a laugh), where the director donated 100 hours of interview footage to the Jamaican Music Museum and the Institute of Jamaica. But finding vintage film of his heroes in their heyday proved elusive.

“There’s almost no old-time footage in Jamaica of ska,” said Klein, who began scouring eBay for “tourist home movies” of Jamaica “without knowing anything about what was on them. I’d just buy them and get them digitized. You never knew what you’d get.”

He wound up with a fairly high hit ratio: Of 25 blind-bought home movies, “16 or 17” yielded usable footage. 

Michaelangelo Matos is a St. Paul-based writer.