Born out of a junior high talent show, Down With Webster has grown into a seven-man hip-hop/pop/rock group that’s been signed to a major label (Universal Motown), headlined its own tour, and just last week was nominated for a JUNO Award for Best New Group.

“We all have really high goals … We want to tour the whole world and do all sorts of other stuff we haven’t done yet,” says bass and keyboard player Tyler Armes. “We haven’t made it yet, but we’re on the right path right now.”

Down With Webster got their start through word of mouth in Toronto, where they played small venues – including the gym of their former middle school – as if they were big venues: banners, red plastic cups, and even a gong bearing their DWW logo have been a part of their show since the early days. Now they sell out 1,000-person venues in Toronto. Having just completed the western portion of their first headlining tour, the band has been branching out to cities they’ve never played before. Though they’ve grown accustomed to big stages – opening for the likes of The Roots, Snoop Dogg, and, most recently, Timbaland – they don’t have any qualms about playing smaller venues again.

“It was so cool to go back to venues where there’s 150, 300, 450 kids and have it be a tiny little room with a small stage again,” says Armes.

Maybe the biggest difference is that they’re playing to their own audience, instead of the headlining act’s fans.

“When you’re opening for someone else you have to kind of accept the fact that those people aren’t there to see you,” says Armes. “When we’re headlining we’re used to kids running up on stage and going crazy and we have their attention from the second we get out there.”

So what does Webster sound like? They’ve got horns like a marching band, guitar solos like the late eighties, and party-heavy rap lyrics between catchy pop choruses. Unlike the majority of hip-hop, you won’t hear a drum machine (unless you count an often-shirtless, afro-sporting maniac behind the kit named Andrew “Marty” Martino). While some songs lean towards the energetic – “Time To Win” and “Parade Music” – others have a more laid back pop feel – “Rich Girl$” and “Whoa Is Me.” Their latest album, Time To Win Vol. 1, maintains a good balance, and a malleable one at that; the band has played for very different crowds, including the Vans Warped Tour last year.

“One of the coolest things that we’ve found since we started touring four or five years ago is that because our music is such a mash-up of different styles, it’s really cool and easy for us to cross over and play for different kinds of music fans,” says Armes. “I think generally speaking people can take away some element of what we’re doing and enjoy it.”

The band has recently returned from filming a special in Cancun for Much Music. Like the 30-second promo video in which the band members are supposedly waking up from their respective blackouts on the beach, Armes only hinted at what went on while they were in Mexico.

“We did the kind of stuff it might take you years to do and did it all in a week,” says Armes.

The Cancun special will air on March 18, in conjunction with the debut of the music video for their new single “Your Man,” a nod to sixties and seventies dating game shows. However, Webster tend to stay in touch with their fans online as well. They’re known for their YouTube videos, including a series of videos of rapper Cam Hunter freestyling (notably at an underwhelmed Waffle House in Atlanta), or Martino tearing through hotels, parks, and city streets banging on whatever he can with drumsticks. The latter perhaps as an homage to drumming legend Buddy Rich, who pulled the same stunt on The Muppet Show in the eighties and remarked “When I play a theatre, I play the theatre!” For Armes, making this kind of effort to connect with fans is crucial.

“You want to let your fans more or less into your life and let them see who you are as people,” says Armes. “It’s not just about seeing your concerts and listening to your CD in your car.”

Known for surprises, like bringing a full drum line on stage for their album release show, what does Webster have in store for Montreal?

“We’re checking out the regulations to see if we can skydive and land in the area right now. [If not] we’ll have to go with the B plan,” jokes Armes. If the B plan is business as usual for a Down With Webster show, you won’t be disappointed at the lack of daredevilry.

Down With Webster plays at the Just for Laughs Theatre on Friday, March 12.