Born-in-Monterey collective Ostrich Head opens for Digital Underground Friday.

This past Wednesday, Ostrich Head’s music video for their super-catchy song “Freak Show Carnival” beat out thousands of other vids from across the country to become one of four Grand Prize winners in the YouTube Underground Contest—which endeavored to find the most talented and entertaining unsigned acts in America.

The Los Angeles-based six-member collective of MCs and DJs, including the soulful singer known as Saywhat? (Lyndsay Haldorson), was flown out to New York City to appear on ABC’s “Good Morning America” with three other artists and received new music equipment courtesy of Gibson Guitar and Epiphone. The video for “Freak Show Carnival,” which features the band members rapping the tune while strutting down Venice Beach’s boardwalk and riding a carousel, will get even more exposure by being featured on YouTube.

It’s a dizzying turn of events for a hip-hop group whose roots go back to a downtown Monterey street corner.

Back in 1997, aspiring MC Nowonder (Steve Montez) would spend his Friday evenings in front of Alvarado Street’s Juice Club, which is now the site of Jamba Juice, freestyle rapping with a beat-boxing friend named RC. Looking back to that time, Montez says he didn’t have any specific goals as a musician. “I was just doing it for fun,” he says.

Despite modest dreams, the weekly get-togethers, which Montez dubbed “Freestyle Fridays,” started to grow in popularity. With more people dropping by to freestyle or just observe the action, Montez moved the event to the open space around the fountain in Monterey’s Custom House Plaza. Meanwhile, handfuls of MCs started forming teams that would compete in rap battles in the park. Montez says his group, which called itself DNA, competed with teams from Gonzales to San Jose in Custom House Plaza. “We kind of became a team,” Montez says. “Other crews would try and battle us, and we would win and take their money.”

Eventually, DNA recorded a tape of four-track songs, which Montez and his crew tried to sell to cars driving by on Alvarado Street. By 2000, Montez’s crew joined with other local freestyle teams to form a collective known as Ostrich Head. The eight-person outfit released a 14-song CD titled Head in the Ground in 2000.

With other Ostrich Head members bowing out, the core of the group became DJ Mes (James Morgan), Loreaxe (Jaime Jorn), Calmentz (Zack Arnett) and Montez. By the time 2002’s Tower of Babel was released, Ostrich Head was performing at local venues like Juice & Java and CSUMB’s Black Box Cabaret in addition to regional clubs including San Jose’s The Usual.

In 2003, Ostrich Head decided to move to Los Angeles to try and kick their career up a notch. “There were more places to play and a better chance of being seen or heard,” Montez says.

Following the move, Ostrich Head picked up two more members: Monterey native DJ Waxbuckler (Tony Calvert) and Saywhat?. Montez says the band had been friends with Calvert for years, but they met Saywhat? when she sang a hook on one of their tracks. “She turned out being a terrific live performer as well,” Montez says.

Since moving to LA, Ostrich Head has opened for hip-hop and rap icons Old Dirty Bastard and Kool Keith along with current star Lupe Fiasco. A year ago, the sextet headlined a show at the 1,100-person capacity House of Blues on Sunset Strip.

The band also just released its latest CD, Shoot the Money, which can be purchased through Myspace.com/ostrichhead. The album features songs like the straight hip-hop of “My Life” and “Long Necks,” which includes a guest spot by Pacific Grove’s The Sauras.

Montez is not really sure how the recent YouTube Underground contest win will affect Ostrich Head. “I would like some forward movement for the group,” he says, “but we just hope to maintain a level of success so we can do this for a living.”

Ostrich Head will be opening for Digital Underground this Friday at Doc’s. Oakland’s Digital Underground burst onto the hip-hop scene with their 1990 debut album Sex Packets. While songs like “Underwater Rimes” and “Doowutchyalike” became underground hits, Digital Underground’s “Humpty Dance,” a showcase for member Shock G’s alter ego Humpty Hump, was a crossover hit on the pop and R&B charts.

The landmark album was known for lifting funk elements from George Clinton’s funk groups Parliament and Funkadelic and combining them with playful, humorous lyrics.

Following Sex Packets, Digital Underground released 1991’s This Is An EP Release. The six-song CD was notable for being the debut of up-and-coming rapper Tupac Shakur.

Since the early ‘90s, Digital Underground has put out a handful of albums, but none have been as popular as Sex Packets.

OSTRICH HEAD AND DIGITAL UNDERGROUND play Friday at 9pm at Doc Rickett’s Lab, 180 E. Franklin St., Monterey. $15/with Ostrich Head flier; $20/without. 649-4241.