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Jason “Filli” Villaroma was a well-known dude on D.C.’s hiphop scene. Heads remember Filli’s rhyming over a karaoke machine or marching through Georgetown with a boombox and starting ciphers. But the thing people remember most about the late rapper is the most uncelebrated expression in all of hiphop: “I’m going to always remember his smile,” says longtime friend Joy Oliver.

In an art that often celebrates cartoonish brutality, Filli was an anomaly—the happy rapper. Even in D.C. hiphop’s diverse pond, finding MCs who want to do more than dis other MCs is like trying to find a supermarket in Ward 8. “When I met Filli, I had a ‘destroy’ mind-set; all I wanted to do was battle rhymes,” says Alan Page, who met Filli while attending ciphers sponsored by the Freestyle Union. “I don’t wanna say he was like the Fresh Prince, but Filli’s outlook was always lighter.”

Filli was a founding member of the Amphibians and one of the organizers of the “Lifeline,” a now-defunct weekly freestyle cipher on U Street. So when news hit D.C. in February that Filli had died of a severe asthma attack, his mourners were legion. In recognition of his contribution to the local scene, several local artists plan to come together this Sunday for a show in Filli’s honor. “Breath: A Celebration of the Life of Jason ‘Filli’ Villaroma” will be a who’s-who of local hiphop, with performances from Unspoken Heard, In Shallah, Defined Print, and Plexus, among others.

Proceeds from the show will be used to start a foundation in Filli’s name that will promote artistic independence and help provide economic security for struggling recording artists. There also are plans to try to put together a nonprofit record label in Filli’s honor. “I wish there had been a better reason to do this,” says Joe Villaroma, Filli’s brother and a credible MC in his own right. “But when [Filli died], everything just changed, and now, with the foundation, we’re on a new mission.”—Ta-Nehisi Coates

“Breath” begins at 8 p.m. Sunday, April 30 at 2K9, 2009 8th St. NW. Call (888) 414-3026 for details.