Andy Cooper's not your average MC, a fact to which many of the nation's hiphop promoters can attest.

"I roll into town and I'll ask the guy, so tell me about this place," says the Ugly Duckling rapper. "And they'll always say, 'Yo man, we got the best bud!' and, 'Yeah, there's three colleges here and the girls are fly!' But then I'm like, 'No, I wanna get some historical background on that cathedral over there, and where's city hall?' After they stare at you with their mouths open for a minute, they realize they don't have to act like tough guys anymore and they can take off the beanie and relax."

Disarming to the hilt, Cooper and his cohorts--MC Dizzy and DJ Young Einstein--have always been content to sidestep the mainstream hiphop tableau of hos, guns, platinum teeth, and decadent yacht parties in order to pursue a more underground, old-school aesthetic. More closely aligned with the experimental creativity and self-deprecating humor of Jurassic 5 and Kool Keith than any rapper you'll see on MTV's Cribs, Ugly Duckling is all about bringing goofy fun and funkified breaks back to the game.

Just like A Tribe Called Quest's Q-Tip and Phife Dawg swapping smooth rhymes about ham and eggs, and the Beasties' name-checking everyone from Sir Isaac Newton to Doris the Finkasaurus, Ugly Duckling's Cooper and Dizzy flavor their tag-team flow with arty eclecticism and off-the-beaten-path allusions. On a typical track like "If You Wanna Know" (from their newly re-released debut album, Journey to Anywhere), Young Einstein serves up bluesy, Fender Rhodes-laced loops and taut beats; Dizzy sings a bar from Soft Cell's "Tainted Love"; and Cooper raps about the trio's anti-violence stance amid references to the Hubble telescope, Herman's Head, and Sha Na Na's "Bowser."

"I keep a big pool of stuff to grab from--just cool words and themes and rhymes and schemes," says Cooper of his writing process. "Some people can get it down really fast, like right in the studio, but I have to take the time to construct stuff for it to work. I like to freestyle but I won't pretend it's any good!"

He and Dizzy also take their lyrical cues from the wax Young Einstein brings in from his countless hours of crate digging, though they frequently take the free-association route in developing their subject matter.

"I'll hear a loop that sounds like something someone would scat over," Cooper explains. "Then scatting reminds me of Mel Tormé and kind of this Hollywood glamour, and Hollywood makes me think of celebrities and the way they try to tell people how to live their lives even though they're hypocrites, so I'll end up writing about that. It's kind of a fun journey for me to do it that way, as opposed to, 'That sounds funky. Let's do it about funk!'"

The inventive results of that approach definitely go over well with the backpack-and-thinking-cap collegiates who compose much of the group's current fan base--they eat up Ugly Duckling's sunny vibes and the genteel mockery of cash-and-gun-flaunting playas, and with good reason. But things were much different nearly a decade ago, when the trio formed in their hometown of Long Beach, California, at the height of the G-Funk era. A colossal example of "wrong place, wrong time," try to imagine three white kids attempting to cultivate a career in positive, lighthearted hiphop at gangsta ground zero.

"Cypress Hill, Dre, and Snoop came along and got platinum success, and it changed everything," Cooper recalls. "It took the people who would have tolerated friendlier stuff like ours away--like, 'Forget that, we're just goin' for tough-guy stuff.'"

Then, as the menacing aggression of gangsta rap gave way to the Benjamin-addled late '90s, Ugly Duckling again found themselves on the outside looking in, despite a well-regarded debut EP, Fresh Mode. So they piled in the van and toured Europe three times and the U.S. twice, gaining a modest yet fervently loyal following across all segments of the hiphop nation.

"We've tried as a group to realize our market and get the respect of that market, and we've anchored down in a lot of places," says Cooper. "We're tight and we do our thing, but we are no geniuses, that's for sure. We developed our abilities, we're a good band, we get the crowd pumped when we play live, and that's good enough for me."