There was a time, according to dub reggae and hip-hop artist Sleepy Wonder, when aspiring musicians had to earn their keep before setting foot in the studio. When Wonder first moved to New York from his home city of Kingston, Jamaica, in the mid 1980s, the city’s underground dancehall scene was booming. Reggae artists from rival sound systems would gather at crowded parties to engage in lyrical clashes onstage, vying for respect and recognition in a teeming talent pool.
“Sunup to sundown, just proving yourself to an audience, and that’s how we made a name in those days,” Wonder said.
On the surface, dancehall music garnered little commercial or critical attention. But, if you knew where the party was, you could access an underground culture with roots stretching back to Jamaica. Sound systems—teams of MCs and DJs representing different cities—would challenge one another in freestyle competitions, entertaining throngs of guests who turned out to see the contest. As word spread, the style caught on, and artists like Sleepy Wonder and his friend Shinehead became local celebs.
“The venues were more like basements at the time. It would be so crowded,” he said. “It moved from there and we started getting into venues with 500 to 800 people, and then we started getting into venues with 3,000 people.”
Now a vocalist for popular Washington, D.C.-based DJs Thievery Corporation, Wonder will perform at Foobar in Portsmouth on Saturday, Jan. 8, where he’ll be joined by Boston’s SuperSka and the Seacoast’s own Green Lion Crew. Presented by WXGR, the show will offer a generous winter helping of ska, rocksteady and reggae.
By the time he started working with Thievery Corporation in the early 2000s, Wonder’s career had seen some ups and downs. He started building up his name as an ambitious young artist in Jamaica, where he adopted his unique moniker (“Sleepy,” he said, because of his naturally droopy eyes, and “Wonder” because he had a passion for playing keyboards, like Stevie Wonder).
“I started doing my thing in Jamaica, so I had a name that was buzzing with underground cassettes,” he said.
In New York, Wonder recorded a couple of singles in the late ’80s before releasing his first full-length album, “Vibes,” in 1988. Wonder found himself in demand around the world, performing in Japan, Germany, France, England, Italy, Greece and throughout the Caribbean.
With his career on the rise, Wonder signed with Columbia Records in 1995, but he never released an album on the label. Looking back, he believes Columbia signed him and other popular dancehall artists simply to prevent them from signing with rival labels.
“They were going around and signing all the immediate threats...to make sure other labels couldn’t have what they were doing,” he said.
Dance label Strictly Rhythm soon bought Wonder out of his contract with Columbia and signed him to its hip-hop arm, Phat Wax Records. There he recorded a single called “Rookie,” which skewered newer artists who dove straight into the studio without sweating through years of dancehall clashes like Wonder and his peers.
At the same time, Wonder wrote songs for and appeared on albums by a number of other artists, including Shinehead, Shelly Thunder and Papa Dee. It was through his collaborations with Shinehead that Wonder came to the attention of Rob Garza and Eric Hilton, the two masterminds behind Thievery Corporation.
The Thievery duo wanted Wonder and Shinehead to bring a New York reggae vibe to their 2002 album “The Richest Man in Babylon.” But it took some time for the Jamaican-born Wonder and British-born Shinehead to get on the same page as the two D.C. natives.
“I didn’t know what they were looking for, Shinehead didn’t know, and they didn’t know how to tell us what they were looking for,” Wonder said. “For two days, we had just different ideas. Then something clicked in my head and I said, ‘I know what these guys are looking for.’”
On a whim, Wonder stood up and sang the melody to what would become “State of the Union,” one of the album’s well-known political protest songs. “(Garza and Hilton) jumped up and said, ‘That’s it!’”
Wonder’s work with Thievery continued on their following album, “The Cosmic Game” (which also features David Byrne, Perry Farrell and Wayne Coyne of The Flaming Lips). Wonder penned the song “Warning Shots,” which later appeared on the “Tiger Woods PGA Tour” video game in 2006.
Wonder was involved in a dizzying array of projects during this period and performed at several major concerts, including Lollapalooza in Chicago in 2006. But his work with Thievery Corporation remained central to his career. He wrote the title track to their 2008 album “Radio Retaliation” and also appeared on the opening track, “Sound the Alarm.” The album was nominated for a Grammy Award for “Best Recording Package,” but the category went to Metallica for “Death Magnetic.”
Now a resident of Virginia Beach, Wonder has also started his own record label, No Choice Music. He released “Injustice,” his first solo album in 10 years, in 2009.
“That album was bits and pieces of me touring all over the world with Thievery Corporation and gathering more information, more fan base, more knowledge,” he said. “I think it was just Sleepy growing up and getting a wider fan base.”
The album is filled with politically fueled songs like “The World is in Trouble” and “March Up in the Hills.” Wonder said gangster rappers and other musicians with violent lyrical content are killing the hip-hop industry. He strives to create music with a nobler message.
“People need uplifting music to listen to,” he said. “There are socially conscious things that need to be addressed.”
Wonder also remains signed to Garza and Hilton’s label, ESL Music. He’s currently at work on a new Thievery album, due out next summer. He’s also developing a new solo album, although there’s currently no timeframe for its release.
Meanwhile, Wonder is looking forward to his upcoming gig in Portsmouth, where he’ll join a couple of regional acts. SuperSka consists of eight veterans of Boston’s ska and reggae scene, including three former members of Bim Skala Bim. Green Lion hosts a weekly reggae night on Sundays at The Red Door in Portsmouth. Wonder said he’s excited to share the stage with a group of new faces.
“I’ve never rehearsed with those guys, I’ve never even met those guys, but I promise you it will be something to remember,” he said.
The show begins at 9 p.m. on Jan. 8 at Foobar, 21 Congress St., Portsmouth, 603-373-8973. Tickets are $8 in advance or $10 at the door. Guests will be eligible for prizes, including free ski tickets.

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