Right now in Chicago there are about 1,200 aspiring improvisers enrolled at the Second City Training Center, 600 at ImprovOlympic, and 100 at Annoyance Productions. Add them to the legions that’ve already graduated from these programs and you’ve got some 5,000 improvisers in the city, many of whom have come here specifically to study and perform. All of them want what Dan Bakkedahl had.

After enrolling in his first Second City class in 1997, Bakkedahl, now 35, enjoyed a rapid rise to the top: by the fall of 2004 he’d been performing on the Second City mainstage for a year. In a month he and the rest of the mainstage cast were to collaborate with director Mick Napier on the 45th anniversary show. He was a phone call away from being hired by Saturday Night Live, Mad TV, or Late Night With Conan O’Brien.

But Bakkedahl wasn’t happy. Drained by the mainstage schedule, he found himself closing down Old Town bars every night. He was frustrated by the constraints of Second City and embittered by a deal the company had inked with Sony Pictures Television. One night during a performance he punched the mainstage wall in anger, breaking his hand. The next week, on the day the mainstage actors were to sign their Equity contracts for the anniversary show, he called it quits.

Bakkedahl left the mainstage without the traditional ceremony and farewell party. Many of his friends and colleagues believed he’d overreacted; others thought he was being selfish. Bakkedahl still thinks he did the right thing.

“There were all sorts of fantastic reasons to stay,” he says. But “the only one that really matters–my heart–wouldn’t let me. And it’s my heart that lets me do any show that I do. It’s my heart with which I improvise.”

Bakkedahl first saw a Second City show in 1995 while he was here touring with the Texas-based Repertory Theater of America. He was under the impression that it was fully improvised (Second City actually uses improv to generate scripts), and he became fascinated with the idea of doing improv. “So I moved here, and it took me two years after doing it to even get the balls to take a class,” he says. In the meantime he performed in several off-Loop plays, including The Kentucky Cycle with Pegasus Players, which won a slew of Jeff citations in ’97, and Pentecost, directed by Warner Crocker at the Theatre Building. During rehearsals for Howl at the Moon at Bailiwick Repertory, a castmate urged him to take an improv class, and he decided to finally do it.

Bakkedahl enrolled at Second City in June 1997 and a year later began taking classes at ImprovOlympic as well. “I was like everybody else,” he says. “I thought there was a mathematical equation to this thing: two years at ImprovOlympic and two years at Second City equals touring company. Two years on touring company equals E.T.C. Two years on E.T.C. equals mainstage.”

Miles Stroth, a gruff Chicago improv veteran who studied under legendary improv guru Del Close, taught Bakkedahl’s intermediate-level class at ImprovOlympic. At that time Robert Dassie, Stephnie Weir, and Rich Talarico (the latter two Second City mainstage players in the late 90s) were doing a late-night show, Trio, at the venue. Stroth wanted his next project to be a two-person show with the breakneck speed that was the trademark of the Family, the influential ImprovOlympic ensemble he’d been a part of in the mid-90s. Instead of asking one of his peers to join him, he decided to pick a student. “I needed someone who was willing to do it my way,” he says.

Stroth’s first choice was Karen Graci (who went on to perform with ImprovOlympic’s featured group Baby Wants Candy and tour with Second City), and when she declined he asked Bakkedahl, impressed by his ability to absorb what he was teaching and play convincing characters onstage. It’s something Bakkedahl’s known for even now. “He believes so much in what he’s doing,” says Jean Villepique, his former castmate on the Second City mainstage. “He’s not even ‘acting’ acting–he’s just believing.”

Bakkedahl was ecstatic. Working one-on-one with Stroth gave him intensive training in long-form improv, the medium championed by Close and ImprovOlympic through what they call the Harold, a fixed framework for improv that alternates between games and recurring scenes. One of the notions Stroth emphasized was what he calls playing the piece rather than the scene. “You start with scenes,” he explains, “but once a few scenes have happened, a show is being created. And you start opening your awareness–I’m not only aware of the scenes I’m in, but how they connect to one another and what pattern they’re creating. You start thinking, ‘How can I best fill in the rest of this show?’ You start playing the piece.”

Most long-form shows have casts larger than two. And while Stroth had been performing improv for about a decade, this was Bakkedahl’s debut. When it first opened in July 1999, Zumpf! barely drew a dozen audience members. “We had two or three rough months at the beginning,” Stroth recalls. “The show didn’t start working until Dan accepted that onstage we were equals. For a while he was still playing with me like I was his teacher.”

Slowly buzz started to build about Zumpf!, and by November they were filling the house. Zumpf! eventually gained cult status–the show was free, but afterward audience members would litter the stage with crumpled dollar bills, which Bakkedahl and Stroth would then use as that night’s drinking money.

Zumpf! deepened Bakkedahl’s growing belief in improv as an art form. “I’ve never done a show as experimental and open-minded,” he says. “I don’t think a lot of people give themselves that opportunity because they’re too busy thinking ‘This is the gig that’s going to get me touring company. Tonight’s the night.’ And I was feeling and thinking the same shit–I just happened to be lucky enough to be with someone who was like, ‘Fuck that crap! You don’t need that. This is the pure art form.’ And that stuck with me.”

Bakkedahl auditioned for the Second City touring company early in 2000. In March, almost a year after Zumpf! began, he got a call asking if he could fill in for company member Greg Mills, who’d booked a TV commercial the same weekend he was scheduled to tour. Second City had informed Mills that if he accepted the gig he wouldn’t be returning to the touring company, but he’d taken it anyway–the money was too good to pass up. Bakkedahl filled in for him and a couple days later was offered a permanent position. “I was like, Yes! Yes! Yes!” he says. “But there was a part of me that felt like, Mills lost his job because of that?”

Bakkedahl got to travel around the country and eventually performed in Saudi Arabia, Kuwait, Bahrain, Dubai, Hong Kong, Japan, Singapore, Thailand, and Bosnia. The touring company introduced him to performers he’d later work with on ImprovOlympic shows like the boundary-pushing Four Square. In 2001 he was in the cast of the opening revue at Second City Las Vegas.

Stroth warned Bakkedahl that the touring company was weakening his onstage discipline. “The whole time Miles was whispering in my ear, ‘They’re poisoning you, they’re poisoning your improv,'” Bakkedahl says. “He meant, Your improv is becoming selfish. You’re going for the gag rather than the real thing.” Improvisers who pander to the audience, going for easy laughs rather than sticking to a character and point of view, “become greedy players,” Stroth says. “A greedy player is out to make themselves look good, often at the expense of the other player, the scene, and the show, as long as they get their laugh in a given moment.”

But Bakkedahl had no intention of quitting the touring company. He was just a promotion away from the mainstage.

Two years later Bakkedahl no longer thought he would be promoted. He’d recently confronted Second City vice president Kelly Leonard after Leonard trashed a show, shouting at him not to speak to actors that harshly. Leonard called each member of the troupe and apologized. But Bakkedahl had had enough. In August 2002 he quit.

Zumpf! had closed the year before, when Stroth got married and moved to LA. So, working with Jean Villepique and Peter Grosz, a friend from his touring days, Bakkedahl put together Unhinged, a Tuesday-and-Wednesday-night showcase for improv and sketch comedy at Second City E.T.C. He also continued to work for Second City Communications, which puts together sketch shows for corporate functions, and taught at Second City and ImprovOlympic.

In early 2003 Bakkedahl and Second City mainstage alum Ed Furman headlined the Tuesday-night show with Trainwreck, a half-hour-long improvised scene. Eschewing the speed and proliferating scenes of Zumpf!, they went for the most stripped-down improv possible: two characters simply arguing, discussing, and brashly emoting.

That spring Bakkedahl approached Second City with the idea of scripting some of the improv in Trainwreck and performing it as a play. He was told that he wouldn’t be available for the project–he’d be on the mainstage by the summer.

Bakkedahl was surprised to feel a tinge of disappointment mixed in with his elation. “The dream just got handed to me, and I was like, Oh, I’m not going to get to do that other thing,” he says. He thought the mainstage shows had changed for the worse since 9/11, becoming more concerned with political and cultural ephemera and moving away from what he saw as more important–fundamental human interactions. “This is not about must-see TV,” he says. “This is about what those two people on the couch are talking about, not what they’re watching on TV.”

Nevertheless, he couldn’t say no. He joined the mainstage troupe in August and began working on a new show in September. But he quickly began to feel that the producers over-steered the production, underutilizing the performers’ individual strengths and stripping them of their integrity. Saturday Night Live and Mad TV have a similar problem, he says: “Both of those shows have incredibly talented people, but the producers are getting in the way. They think they know how to do it, and they don’t realize that they’ve hired a bunch of experts in the field.” Still, Doors Open on the Right opened in December 2003 to good reviews.

Every night after Second City’s mainstage show, the cast does a free set of actual improv. It annoyed Bakkedahl that some of his castmates took these shows as opportunities to let loose, have fun, make the audience laugh. After all, this was their chance to highlight their art form. He thought it was important to focus on creating believable characters–even when they were ugly. “Hitler thought he was right,” he says. “He didn’t walk around going, ‘I’m sorry, I’m sorry.’ So whatever character you’re playing has to think they’re right, or at least think they’re a good person.”

The cast of six was always in flux. Jean Villepique, who was hired at the same time as Bakkedahl, says, “You have a perception of what the job is, and the reality is very different. The perception is that the ensemble was together all the time. The truth is, people are in and out all the time. The longer we ran the show the rarer it was to have the six people there.” In early February cast member Liz Cackowski was hired to write for Saturday Night Live. Cackowski’s understudy, Maribeth Monroe, was on tour and unavailable. Lisa Brooke had gone home to Toronto. Villepique says the instability is one of the things that make it important for her to keep the mainstage separate from the rest of her life: “If you put a lot of drama into it it’s going to give it right back at you,” she says. “If you keep your life out and just go in and do your work, that can be a smoother ride.”

Bakkedahl was drinking a lot. When he’d started doing improv he’d have a couple after a show to unwind and talk shop with fellow performers. Now, performing six nights a week, “I started using shows as an excuse to drink,” he says, “as opposed to what I used to do, which was, I’m here for a show, so I’ll have a drink.” Toward the end of the run of Doors Open on the Right, Bakkedahl made sure that the bartender had a beer and a shot waiting for him at the end of the night. Then it was time to hit the taverns.

Except on Sundays. After Bakkedahl’s last performance each week, he’d go back to ImprovOlympic and put on a show with Grosz and two other friends from the touring company, Rob Janas and John Lutz. Over time Four Square, which Bakkedahl describes as “four warriors following one another,” gained the same cult status as Zumpf! It was his favorite part of the week.

Shortly after Bakkedahl was hired for the mainstage, Second City made a deal with Sony Pictures Television that gives the company the option to develop any material generated by ensemble members, whether it be sketches, characters, or songs. If a network ended up using Second City material, the members responsible for it would split a small portion of the profits. There was also what Jason Brett, president of Second City’s television and film division, calls a “talent-holding deal” guaranteeing select ensemble members consideration for any pilots Sony pitches. “It gives Second City an opportunity to have a powerful partner who has influence with the networks and views Second City as a creative resource,” he says.

Bakkedahl was less enthusiastic about the arrangement. He was already unhappy that the cast created shows for free–ensemble members are paid for performances, but they’re not compensated for material-generating rehearsals. Now he was upset at the thought that Sony could use and profit from his work. “How do you feel about busting your ass to create something that you don’t get paid for,” he asks, “that Sony then also owns, that they can hand to any other actor they want and send them anywhere they want with it, and if it gets picked up you’ll make a little chunk of change?”

This past fall as part of their “talent-holding” arrangement, Second City and Sony put together a showcase and invited certain cast members from the mainstage and E.T.C. to audition for it. Those who made it would perform Second City material for television executives and development teams in Los Angeles. Second City offered Bakkedahl an opportunity to audition but he declined. He felt the Sony deal was an empty promise–even if his characters or material were picked up, he could easily be pushed aside for someone famous. “There was really no way for us to be protected” as performers, he says. “We weren’t guaranteed anything other than the fact that we’d be in the pool of people considered.”

Brian Boland and Maribeth Monroe, two of Bakkedahl’s castmates, were chosen for the showcase, and the scene selected for them was one that Bakkedahl had written with Cackowski. “She and I improvised it, it was caught on tape, and we reproduced it,” he says. “Two of my castmates were now going to take my scene that I wrote on a showcase that I had no liking for, and I was never even told.”

Bakkedahl says he found out backstage one night when he overheard Boland and Monroe whispering about the scene. He asked them what they were talking about and they told him they’d just found out they were going to be performing his piece. Bakkedahl had of course known that anything he created could be used like this; still, he felt it had been done behind his back. “I had to go onstage, unfortunately, at that exact moment,” he says. “I went onstage, tears in my eyes, in front of 300 strangers, doing the yuk-yuk show, and I almost fucking died. It was over.” As the lights faded at the end of the scene, Bakkedahl walked to the upstage wall and punched it three times. He finished the show with a broken, bloody hand.

Over the next several days he talked to Second City producers Robin Johnson and Andrew Alexander, asking them to either pull the scene from the showcase or give him the night off on the day his castmates would be at the showcase in LA. They refused. A week later Bakkedahl sat down to sign his contract for the 45th anniversary show. “My head was spinning, the contract was spinning in my eyes,” he says. “And I’m like, ‘I can’t do this. I’m sorry.’ I crumpled it up and I walked out.”

Red Scare, Second City’s 45th anniversary show, opened in December to laudatory reviews. It “has dramatic passages as strong as anything in a ‘straight’ play and songs as intelligent and well sung as any in a contemporary musical,” wrote Albert Williams in this paper. “And while comedy dominates, . . . it transcends the shock-jock cynicism director Mick Napier has sometimes employed in the past, aiming instead for a riskier kind of humor that doesn’t always culminate in punch lines.”

Napier, who directed Bakkedahl at Second City Las Vegas, admires the performer’s work. “I think he’s a better actor than he even knows he is,” says Napier. “He possesses a rough truth about things, a kind of no-bullshit demeanor when he improvises.” He says he wishes Bakkedahl had been part of Red Scare. “I was very disappointed,” he says, “but I know that one has to make integral decisions in their lives, and that was one of Dan’s.”

Villepique was also sorry to see Bakkedahl go. “I know that Dan left under circumstances that were not happy for him,” she says. “But I respect the fact that he said, ‘This is not me. This is not right for me. I’m done.'”

Bakkedahl’s back at ImprovOlympic now, teaching classes and performing. He and Furman have resurrected Trainwreck, and he’s in Play, an improvised show with a cast that includes Grosz and fellow mainstage alum T.J. Jagodowski that opened last month. He’s also auditioning for straight plays. He calls quitting the mainstage the best thing he’s done so far in his career.

“I began to realize that in this business, in the specifics of sketch and improv, there are two kinds of people,” he says. “Those who are in it for the art form, to further this thing and be part of this thing, and those who are in it to get that next gig. I think I used to be fifty-fifty, and now I know I’m fully on the art form side.”

Bakkedahl’s stopped drinking since leaving the mainstage. “Since I’m being honest about this job being bullshit and something that’s not good for me, I figured I was going to be honest about something else”–namely, that his drinking had gotten out of hand. “I don’t need anything in my life that’s not good for me,” he says. “It’s going to be the Dan show from now on. I’m going to be calling the shots in every aspect of my life.”

He has a few words of advice for all those improvisers struggling to make it. “Everybody’s busting their ass to get on mainstage,” he says. “There are only six spots. So fit one of those roles at the exact right time, and maybe it will happen. In the meantime, enjoy your fucking Harold show, because you’re wasting your time thinking about that shit. You’re already doing it.”

Art accompanying story in printed newspaper (not available in this archive): photos/Jim Newberry, Michael Brosilow, Adam Jacobs.