Bobby Crane is slapping high-fives with the dozen or so comics hanging outside the downtown Comedy Works, Denver's thirty-year-old comedy club, on a balmy Tuesday evening. Many of them are waiting for New Talent Night to begin, but others, like Crane, have recently been promoted to the club's middle-tier level and are signing on for a possible slot on the headlining show later that night. If Crane gets the gig, it will be the fourth venue at which he performs tonight.
But for now, they joke and wait, sipping coffee and discreetly passing a joint. "Up until recently, before I quit my job, I was only doing two or three shows a week," the 27-year-old Crane explains, holding a hit of smoke in his chest as he talks about giving up a Vine Street Pub paycheck in order to work on his craft. "But Sam was doing like seven shows a week. He was already good, but he just kept getting better and better. I knew that if I wanted to get better, I needed to do more shows. I'm not rich, but I'm supporting myself on standup comedy now."
When he was growing up in what was then a Latino neighborhood in northwest Denver, Crane's only exposure to standup comedy was on family vacations, when the novelty of cable TV in motel rooms introduced him to the sinful world of Comedy Central. "After my parents went to bed, I'd watch standup and think it was the coolest thing in the world. I remember thinking, 'This is like a sitcom, without any boring lesson.' Years later, when I went to college, I got really into it and started buying comedy albums. But I didn't realize there was local comedy that you could go see."
Walking down a hall at the University of Colorado Denver in 2005, Crane came across a poster displaying a pantless Santa Claus sporting a snug thong. It was promoting Los Comicos Super Hilariosos, an underground event featuring a group that would come to be seen as the senior class of Denver comedians.
"There's something to be said for a live performance," Crane says, remembering his first Denver comedy show. "You can listen to an album and chuckle, but when you're seeing it live, it hits harder."
After catching that show, Crane learned of an open mic that Los Comicos member Greg Baumhauer hosted at the Squire Lounge. The Colfax bar's weekly show had developed a reputation as a no-mercy boot camp for would-be comics, a place where, if the drunk, distracted, often heckling crowd didn't crush your will to ever stand on a stage again, Baumhauer's unforgiving jabs as the emcee might.
"Comedy is not a nice business," says Baumhauer. "And comics need someone who is honest. The Squire was a mean environment. It was a battle, and if you could last there, it got you ready for what was to come."
Baumhauer explains this while sipping whiskey at the weekly open mic at the Matchbox, a less harsh but widely respected comedy show where a good portion of the audience is made up of local comics. Dressed in a red velvet suit with a ruffled white shirt and sporting a pencil-thin mustache, he is currently in his Bobby Valentino character, a crude-talking lounge singer with the mouth of Tony Clifton and the antiquated style of Gomez Addams.
The Squire's legendary status as an unforgiving gauntlet intimidated many young comics, but it also weeded out the meek from the strong. Los Comicos members Adam Cayton-Holland, Ben Kronberg and Ben Roy (who have gone on to perform on Conan, Comedy Central and Just for Laughs, respectively) would hold court in their own booth at the back of the bar — and an invitation to join them after a good set was the Denver equivalent of being waved over to Johnny Carson's desk.
"I went to the Squire every night for a year and a half before I ever signed up to get on the stage," remembers Crane. "I was only nineteen at the time, but I got a fake ID so I could go every week, just to watch Kronberg, Baumhauer and people like Chuck Roy and Josh Blue, who would drop in. I couldn't believe comics this good — at times as good as the albums I was listening to — were performing a half-mile from my apartment."
And once he did get on stage, Crane started delivering conceptual material that often confused audiences — either temporarily, with a joke that needed time to sink in, or permanently, with one that would simply bomb.
"I knew he would be good after the third week he was up there," says Baumhauer, taking a heavy pull on his cigarette. "For being so new, he was pretty impressive."