This Friday night is going to be busy for Hamilton drummer Greg Santilly. At the same time that he appears on the David Letterman show in New York City, he’s playing at the Empty Bottle in Chicago.

Actually, the Letterman performance is being taped tonight. The Chicago gig is live, and when it’s over maybe the band can get somebody with a PVR to show them how things looked back at the Ed Sullivan Theatre.

And then, of course, there’s that appearance on the Leno show Nov. 7.

Santilly is 29, modest and grateful for the fast, transcontinental ride he’s been on all this fall.

In Grade 7, for Mr. Johnson at Dundas District, he produced a book called Makin’ It Big, which was about doing just that in the music business. (His mother Evy saved it and it’s on her Facebook page right now.)

Santilly ended up teaching drumming at Avalon Music in Dundas, 35 students a week. But five years ago he saw that a band called The D’Urbervilles were looking for a new drummer. He auditioned, got the job.

John O'Regan and Greg Santilly met about five years ago when Greg answered John's call for a drummer. (Courtesy Colin Medley)

That band, with lead singer John O’Regan of Oshawa, morphed into another group called Matters. Then the guys went on to other things.

Santilly’s been playing around town, including weekly appearances at Gallagher’s with the Born In The Eighties cover band that always packs the place.

But he pays the bills by being a self-contracted medical-supplies courier. He does it in style in a mean Dodge Magnum wagon, midnight blue, heavy tint, 20-inch performance wheels. Good for the job, good for gigging.

But one day this past summer, he got an e-mail from O’Regan, that former band mate. He’d been doing well, got a contract with major label Astralwerks, and he was recording as Diamond Rings.

He had a job, opening all across the States for a Montreal pop band called Stars. And he needed a drummer. They’d be going to Boston, Washington, Atlanta, New Orleans, Dallas, L.A. and a few dozen other places and they’d be gone three months.

You don’t get a message like that popping up on your smart phone every day. Santilly talked to the people he works for. "Go for it," they said. "You’ll have a job when you get back."

That's John O'Regan in bright white up front, Greg Santilly at far left in special-ops black. (Facebook image)

It began in Montreal on Sept.19 and they’ve been running hard ever since.

It’s half-a-dozen people in the van, captain’s chairs for all. Each morning begins at a hotel not far outside the place they played the night before. Wake-up could be anytime from 8 a.m. to noon, depending on how far it is to the next city.

The boys will dip into the continental breakfast, then drive off. At the next city, it’s set up and sound checks.

That done, Santilly gets out his iPod, finds some free Wi-Fi and locates the nearest skate park. He grabs his board and rolls over to it, maybe a couple of miles away. "I meet the locals, take a few pictures," he says. Wildest park so far – San Diego.

The show usually starts around eight. And up there on stage, fans going wild up front, Santilly keeps his cool – as usual. "I’m kind of known for saying, ‘No big deal.’"

John O'Regan, aka Diamond Rings, has just released a new album called Free Dimensional. (Courtesy KCRW)

And he wants us to understand who this show is about.

"It’s all John," he says. "Diamond Rings is John and we’re the back-up band. He’s on the phone every day doing interviews."

Santilly had a three-day break in San Francisco this week and was joined by long-time girlfriend Jennifer Moore, who edits by day and serves at the Lazy Flamingo by night. She got to see him play a sold-out show at the legendary Fillmore.

The tour changes now. O’Regan had put together a studio album called Free Dimensional, and it was released this week. Diamond Rings now becomes the main act for the rest of the tour.

It will push up the California coast and then through every major city in Canada, ending in mid-December. The date Santilly looks forward to is Nov. 30, when Diamond Rings hits Hamilton, a Friday night stand at This Ain’t Hollywood on James North.

A practice session this summer before the long road trip. (Courtesy Colin Medley)

But right now, there’s Letterman to think about. They’ll be doing one song – I’m Just Me – and it’ll be Santilly in black doing duty on electronic drums and back-up vocals.

"I just want to play that one song the best I can and make no mistakes," he says. "It’s an honour to tag along and have fun."

Don't want to wait for Letterman? Click on the video below .

Paul.Wilson@CBC.ca | @PaulWilsonCBC

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