written by Ken Carlson

“I was hosting a July 4th event at the Washington Monument in 2001. They had just finished restoring it. I was just supposed to keep it light; some humor, some public service messages, while the bands were changing out. They had a variety of acts. They didn’t tell me that the bands would take much, much longer to change than advertised. So, I was out of material by the second break. I thought I had to do an hour, maybe an hour and fifteen minutes. It turned into two and a half hours. I was reading pamphlets. I thought it would be families. Instead it was young guys on towels getting drunk, waiting for fireworks. They were getting meaner and drunker and the sun was baking down on us. It was just awful. They were getting really hostile. I would read them trivia and all I could think was that all between me and this angry Woodstock crowd was this little picket fence thrown together by little pieces of wire. That wasn’t going to protect me at all.”
For all the comics I speak with and all the hell gig tales they spin, the one thing I never get over, is how remarkably easy it seems that a situation can go from a casual easy-going public gathering, to an angry mob of medieval beast-hunting peasants that suddenly rise as one with torches and pitchforks shouting, “Kill the comic! His sense of irony and satire differs from mine!” Such is the life chosen by Jeff Caldwell, a headliner whose smart style of stand-up has made him a favorite in clubs, brought him success on the corporate circuit, and televised performances on ‘Late Night with David Letterman’ and ‘The Late Late Show with Craig Ferguson’. I sat down with Jeff recently at the White Horse Tavern.

“My first open mic was in ‘86. I started getting paid in the springtime of ‘87. I’ve been full time ever since. It didn’t make a whole lot of sense, but I decided I was going to do it.”
“I remember being terrified at the beginning. There’s nothing like public humiliation. I think that’s a special level of humiliation. To have people say, ‘You’re awful.’”
“I was shaking, the lights in my face. I think some people have confidence from the beginning. For me, it’s taken years to get to where I’m comfortable on stage and can speak without being terrified. What a thing to be up there.”
“It was a great atmosphere. It was in Baltimore where I was living. The club, Charm City Comedy Club, where I got my start would bring in acts from Letterman and Carson weekly. So, you could learn from really savvy pros. The club’s still there and does some comedy. I know one of the part-owners, Bob Somerby, one of the wittiest people I’ve ever met. It was a great place to learn. I was so thrilled when they asked me to MC the weekends. They had (Paul) Reiser there early on, Paula Poundstone. Bill Hicks was there a few times. Kenny Rogerson, one of the really good acts at that time.”
With two decades spent on stage, Jeff, like most comics, look back at their early days and wince. I asked Jeff about his early shows, what mistakes he made. “All of them. I was terrible. Dreadful. Really dreadful. I didn’t know how to write a joke. I didn’t pick topics that people could relate to. I wasn’t terribly funny. I don’t know how I managed. Eventually, I got skilled at audience work. It’s only in the last five years, that I’ve got a really good body of material. It’s such a slow process, well, for me it was anyway. It’s something I get better at all the time; crafting jokes, connecting with people, hitting them where they’re interested. On the road, it’s still... I just finished a week at a club in greater Indianapolis, well, lesser. It was such a struggle. They (the owners) thought it was fine. They wanted to do it twice a year. But I thought, ‘This is just not fun. I’m not the kind of act they enjoy.’ I think they would’ve much preferred a man strumming or juggling. There would not have been many who were less suited to that room. I did well enough. I told them, ‘I don’t think we should do this again.’ I didn’t want to insult their room, but the audience and I just didn’t mesh.”

“I do what I have to do to make the dough. The trend is good. There are more theatre shows, more corporate shows, and fewer clubs that I don’t want to do so I’m able to pick my spots a little bit more. This year, I’ve quit the cruise ship world. The money was fine, but the shows were never better than mediocre. All I have in the way of control, is putting myself in places where I might succeed. It’s good not to have to take every crap gig that comes along. You have to start saying no to stuff, even when your every instinct is that you can’t turn down any money.”
For someone labeled a clean comedian and a smart performer, Jeff actually flies in the face of his industry. Does it make you a bolder performer if you swear constantly and use offensive material to get laughs or forego that route and succeed just the same? Should a comic get a CD of his material out there simply because he can? What is the job of a comedian, to take a stand or make you laugh? For every time-honored rule you hear and read about, Jeff Caldwell, engineer-turned-jester, seems to think the opposite. He takes nothing for granted. His standards are high with regards to humor, both his and others.
“I know some people who say all stage time is good. I do not believe that. Some stage time makes you worse. There are some situations to succeed is to do really bad comedy; dumb, dirty comedy; stuff for people who are only using the brain stem; aggressive stuff about sex or excretions - the real reptile basis. That doesn’t appeal to me. I know now where I’m apt to succeed and where I’m not. I try to be more selective. At this point, I’ve been at it so long, I need to make time count. So, I’m trying to be smart and savvy about where I work.”
“Although I wish it were different, metropolitan is a great way to describe it (his appeal). Those rooms suit me best. Other rooms, it’s just too much like homework for them. I think the jokes are really good and getting better all the time. But, some people just cannot tolerate 45 minutes of that. So, there are some rooms where I’ll be nothing more than a serviceable middle and I’m not going to do that.”

“Jeff is one of a handful of comedians working who can hold the often scatter brained attention of an audience without talking faster, louder, or swearing. It requires a confidence and quality of material that I aspire to. The first time I saw him perform I became an instant fan. At the same time, I also had to become more critical of my own work to try and keep pace with him. He's one of my all time favorite people on and off stage.” – Gary Gulman, comedian

“Bill (Hicks) was a great example of a guy who could crank it up and make it dirtier or make it really political in certain situations. He could get by, even though it was very clever stuff, being incredibly filthy. That would buy him a lot of credibility in Fife (Alabama).”
“I remember him saying at one point he didn’t want to be called a comedian anymore because Howie Mandel was a comedian. Bill wanted to be a revolutionary poet. He was out of place. He could do the club thing, but I think he just moved on. When I first saw him in the late 80’s down there in Baltimore, he had such well performed stuff; silly in places, strange tableauy material about his crazy family down there. I think I missed that when he moved on. It was funny. I kind of liked that slice of weird Texas life.”
“He (Hicks) was pretty eclectic. Then again, he could make people walk out of a variety of rooms. I remember down in Raleigh, you couldn’t hear him with all the chairs scraping with people fleeing. His bit about the anti-Christ, shitting out Wham or the Brittany Spears of the time; it had a lot of word play but it really infuriated the crowd. While he could make people really happy, he could infuriate them. I’m sure club owners weren’t sure which Bill was going to show up or what was going to happen.”

“I think there’s something amazing about a live comedy performance. You can’t quite capture it on TV. There’s that extra sizzle when someone makes a clever aside to the audience and it’s different than the material they’ve heard before. Of course, seeing someone live, there is that starstruck element. It’s an amazing thing. For me, seeing live music still has that quality to it. When I did Letterman, I walked into the Green Room, and there’s Elvis Costello and Tony Bennett. They had done their taping earlier in the day. I think it really helped me because I got a lot of nerves out just talking to Elvis. After that, the show was just, well... It was great!”
Visit Jeff’s website, standupguy.com, too see footage from his appearances on Letterman and Ferguson. It’s a clinic. His timing is solid, every syllable is there for a reason and his persona is engaging. He plays to the camera but still reaches the audience. It’s also interesting to see him do well before a large crowd when everything goes according to plan and a small crowd when everything doesn’t. “I was really furious at the Ferguson thing. They had changed the air date and I had only five days notice. I had that election thing (topical material) right up front. I was telling this election joke a week before the election so it made sense to people. But the episode was going to air a week after the election. I had to rejigger the wording. You know, the last thing you want to do when you have a set memorized, is worry about getting the words right in the opening joke. So, (on Ferguson) I looked at my body language; I didn’t even move my hands until about minute three. At that point, I realized every thing’s OK. But, with Letterman, I enjoyed that more. They were such a hot audience. It takes all the pressure off. They were right there, right away. With Ferguson, it was my second time there. I had forgotten how small the room was. It holds maybe thirty people. It’s often the people who couldn’t get on ‘The Price is Right’. The Letterman audience wants to be there. They’re committed. I thought the Letterman crowd was just perfect. I think they were a little bit hungry because Nathan Lane did two segments before me. The first segment was OK. I’m not a huge fan. The second segment, I thought, dragged. Then, he did a taped comedy piece which was just awful. Excruciating. Dave was making faces when we came back from that. I think the crowd was thinking, ‘Are you kidding me?’ So, they were really hot from the moment I started. When I walked out there, I didn’t know what I’d remember. I knew the first joke and I hoped it would roll from there. But the crowd was so good, it took all the pressure off. I think I enjoyed that more. I was kind of annoyed by the Ferguson one.”
“I definitely did some practicing at home, just trying be natural with the hands. They (Letterman) don’t even offer a mic and a stand. They just say you’re going to use the lapel mic. On Ferguson, I think there was a choice, but I had done Letterman shortly before that so I said, ‘Let’s just do it this way.’ Your face is unobstructed. You can do it right to the camera. Maybe casting people like that. I don’t know. I did a lot of work beforehand, trying to be loose. At first, I looked like a mummy. Eventually, I got a little looser. I knew from previous cable shows, anything different than what you’re used to will come out at the moment when you’re so nervous. So, I like to get all the angles out.”
“What was helpful with Letterman, Eddie Brill was really good about walking me through what to expect, where my spot was. I came in a few days before to watch a taping. He said, ‘You might want to consider telling your jokes to the camera man. In the clubs, you want to scan all the people. It doesn’t look so great on TV.’ So, if you tell it to the camera man, your connecting with someone, and also getting your face on TV. That was really helpful. I was quite grateful to Eddie for taking the time. He’s done it for years so he knows what he’s doing. He was really considerate and very helpful with the whole process. He’s a good guy.”

“I got my bachelor’s in engineering at John’s Hopkins. I wanted to be an environmental guy; to save the world. The only job I could get was designing sewage pump stations. I stuck with that for about ten months. Then, I thought about grad school; someplace to land. Hopkins took me which was great. So, I went back there for two years. Then, they wanted my PhD thesis. I thought, ‘This, is not going to happen.’ I knew a Japanese grad student and he would come into my office and I’d be reading a novel, like ‘The Great Gatsby’. He was shocked, saying, ‘You have time to read a novel? Why you not working?’ It irked him to the core. It was true. I was just trying to escape. My math was not good enough. These guys were really brilliant and technical mathematical people. I was good enough to get in, but not likely to get any better. I had started doing open mic’s. Then, I started getting paid. I just stopped going back to school. They may still be expecting me.”

“I really love comedy. When I saw that there was this whole industry, it was a revelation to me; that there were open mic’s. I had been watching stand-up at home when I was a kid. I remember when Johnny Carson was on, I would hold my little tape recorder and microphone up to the television and tell my family to shut up so I could catch what he was saying. I never thought it was possible to do this, but then there were these open mic’s. It was right there in Baltimore. I tried it and was terrible. I struggled to get the nerve up to try it again. I guess I was just stubborn.”
“I feel competent now. Within the last five years, I’ve found that I know how to write jokes; smart jokes that smart people will enjoy. That’s something I get a lot of feedback from on my website, this feeling that people didn’t know comedy could be like this. I think people have sort of given up on comedy; not that I’m some sort of savior (though his initials are J.C.). I think there’s an under served element out there because the industry is skewed so young. It’s so dirty and explicit. Not that there’s anything wrong with that. It pleases a certain segment. But, I think there are a lot of adults who want something else and aren’t getting it. I am encouraged by people like Bill Maher, Al Franken, Stewart & Colbert.”

“(The pressure’s) never off in this business. I had a sitcom development deal in 2002-2003 with CBS. They wrote two scripts for me. One which was really great and I’m very proud of it. It didn’t get picked up. While the process was going on and being considered, my writers, guys from ‘Cheers’ - smart, funny guys that I really enjoyed working with, were so confident. I’d ask, ‘Are we going to get on the air?’ They’d say, ‘On the air? It’s just whether we get a whole season or not.’ And, we never got on the air. During that time, I had such an increase in industry presence and awareness. I was on people’s radars. I was getting auditions that I never would’ve gotten before. It was a huge step up in industry credibility, not that I had gotten any funnier, but someone had seen me at CBS.”
“That went away. But, starting in 2004, I did the Dennis Miller Show. In 2005, I went to Montreal and did the Masters there and did a Ferguson spot. In ‘06, another Ferguson and a Letterman. I feel like I’m in the mix again. I was worried that I had had my shot. But, I don’t feel secure. I see some people, like Brian Regan. I’m so happy for him. Now, he’s blowing up like he ought to have years ago. It’s important to me to see someone who keeps plugging away, didn’t get the sitcom, but people have taken notice. He makes a lot of dough, I’m sure, and I think that’s great.”

“I think the premise is wrong (on the necessity of making a point). I think the job of the comedian is to make people laugh. I think it’s great when people also say what they think, but you have to pick your spots. Bill Maher and Al Franken have cultivated their audience. Now they can do what they do. But if Bill Maher was in a bar and named Joe Smith, he’d be run out on a rail. It wouldn’t work in Greenwood, Indiana. I know Bill did clubs for many years. I remember in Baltimore, he would have trouble some times and get snotty with the crowd because they didn’t like his perspective. But, now he’s gotten to the point where he can say what he thinks. He’s got a stable of brilliant writers that are producing stuff with that Bill Maher brand. I think that’s terrific. I think that’s the ultimate goal; to develop my crowd who want Jeff Caldwell stuff, and just do it. But, I’m not at that point, so I have to see what the market will bear. The DC Improv, where I can do a lot more because the crowd is bright and into current events, they know the information which is the basis of the joke.”

“I’ve tried sitting at the desk and writing from nine to five. It doesn’t work especially well for me, unless it’s topical stuff where I’m perusing all the different websites and gleaning tons of information. For my act, it might be something that somebody will say or something you’ll see that just tweaks you, that it might be funny. It’s just instinct now. I’ll try that and see how it goes. It’s not sitting and cranking. I usually have it fixed when I take it to the crowd. Sometimes if you start riffing on it with the audience, things will come to you. It’s usually just trial and error. If they shoot it down, tweak it and try it again. It takes a fair amount of revision and it’s a slow process. About 5% of the material I write down turns out to be anything good. I’m sure some others have higher success rates.”
“I would love to write for Stewart or Colbert, Franken or Maher. Those guys to me are doing the best stuff now. I’ve done odd jobs (writing). I did a punching-up thing for a Discovery Kids show where they wanted humor for a kids show about animals, ‘Zak’s Ultimate Guide’. It was fine. It was a paycheck and fun to be in that world. But, that’s an unusually competitive field. Another thing that’s very hard, is when you’re on the wrong side of 40. It’s almost as youth-centered as performing. So, to me, do I want to spend all that energy, to break into another field? Maybe I should just stick with the one I’m in. I know the Letterman people really like me. I met with the Worldwide Pants people about sitcom stuff three weeks ago. I’m hoping maybe someday there will be some sort of relationship there.”
It was at this point, that Jeff turned the tables and asked me a question, “Do we have enough questions left for another round?” Yes, we did.

“This is my (Jeff’s) CD. It was recorded just over a year ago. It’s just not good enough in my opinion. There were audio difficulties that would require thousands of dollars to fix. Something about the show didn’t really catch fire for me. I wasn’t loose enough, the laughs were serviceable. It was fine. I hate seeing other guys putting out CD’s just because they can. This is your signature piece. I think they’re thinking short term. I think they want something to sell at shows to make a few dollars, which I can completely understand. But, this document about this stage of your career is out there forever. It just isn’t worth it at this point to not have something your proud of. I know you can become obsessive and worry about this forever, but I’m sure we’ll get some level of show that I’m proud of. We’ll get it, but it’s just not that. It pains me to see some young guys, who crank something out because they want product.”

“I was lucky to work with Jeff for several years on the road – West Virginia, Kentucky, among the many stops -- where audience members would frequently say to me, ‘I wish there were more comics like Jeff.’ There aren’t many Jeff’s out there because one of the things that sets Jeff apart – the quantity and quality of really good jokes in his act – is such a hard commodity to come by.
His premises always begin in a real place, the punchline is never later than the second line, his taglines -- he doesn’t use many – aren’t for color so much as they are second and third punchlines.
With Jeff you don’t get angst, stream of consciousness, a view into an internal world fraught with insecurity. You get a new version of Everyman – college educated, progressive, and self effacing, comfortable expressing the challenges and foibles of technological and scientific progress. You get linear joke writing, an economy of language and precise fresh imagery. It’s smart, funny classic stand-up delivered at spoken word decibel in a voice that keeps up with a daily life of accelerating change.
For so many years Jeff went relatively undiscovered. I would read articles about contemporary comedy -- how it was full of sound and fury but “where are the punchlines?” and I would think have you seen Jeff Caldwell?” – Brett Leake, comedian

“It’s like walking a tightrope. There are so many ways for it to go wrong. I don’t know how to describe it. There are so many different variables. I’ve learned not to get in my own way. A lot of the time, I’ve decided beforehand, ‘Well, these people are going to blow.’ So, I get clenched and defensive. I just put it out there. For me the best shows are weeknights. The people who go out on weeknights tend to be smarter, more cosmopolitan, more interesting people. Weekends can be dumbbell date night, ‘This is what we ought to do.’ No imagination. Those are often the only shows at DC Improv I don’t like. You hear it from the smoking section, and they just wreck the whole show. To me, I’m not the most accessible guy in the world. My proportion of mediocre to bad shows is higher than some. Some guys are just money every time they go out. Every time I see Butch Bradley, he’s going zero to sixty, cranking it out. That, to me, is quite a skill. The guys that I’m really like, we have to find our crowds because it’s a little more thoughtful, a little more subtle. Some people just find it tedious, like homework.”
“In a club, I’m thinking about my openers, what my first five minutes will be like. That’s often when I’m trying to connect through local stuff, topical stuff, all the sort of new untested things right up front. The rest of the show is locked down in the memory bank. I watch the whole show. A lot of comics don’t. I like to know what’s happened before. There are references you can make. There is information you can use.”
And what is life like on the road for this veteran comic. Non-stop partying? Trashing hotel rooms with groupies? Starting barroom brawls with Mark Russell? “It’s pathetic. I read and watch sports. I think I’m known as the comic fastest from the stage back to the hotel or condo. Nothing good can happen except spending money. When I was single, it was great. There are lots of young women there, and they all think comedians are neat. I don’t need that anymore. I tell the jokes and get out of there. That may hurt me. Often, the guys who get most popular in the club hang around and have drinks with the manager, or take the bar staff drinking. I’m not opposed to that if it feels natural. I know some comics go in as part of their marketing plan to take the staff out after the Sunday show. It just feels so forced. I feel like I should just do my job on stage. If they like it, they like it. If they don’t, they don’t.”

“I did a show a month ago at Rascal’s in Montclair, New Jersey, a room where I’ve done great in the past. Now, I’ve had a lot of trouble with cops. I’ve done various cop shows and they just hate me. And I hate them back. It’s not that I have any trouble with the law. They seem like these insolent dumb kids from shop class that you were kind of afraid of. They make lots of smirky comments, totally disrupt the show and are disrespectful. This time, I got mad. I haven’t gotten that mad in a while. It got really tense. It just wrecked the show. Normally, I try to say something clever based on what they said. Be gentle, but make them look a little silly. This time, I just said, ‘Are you guys going to shut up?’ Our eyes were locked and I felt myself puffing up. It was ugly and stupid. It was the rage taking over. The managers were working on what to do if something went down. Then, I told a joke that got a few laughs, got off the stage, apologized to the next act, and got the hell out of there. It was shocking. I always think I’ve got a handle on this sort of thing. Then something happens and you find out, ‘Yeah, they can really get to you.’ They were such a large part of the audience and the focal point of the room. Everybody else was dispersed around them. But, they never coalesced with the people who were for me. So, it was just me and them. Often, if you have a goofball in the crowd, other people are happy you’re letting them have it. In this instance the crowd became bystanders just watching. It quickly evolved into something that wasn’t a show anymore. Usually, you can tease them and move on.”
“For corporate gigs, I do my research on their website which is very helpful. They don’t even realize it, but there is so much jargon on their website. Often I will just read them what’s on their website and it’s gobbledy-gook and they’ll laugh. That’s an easy way to start. Then I can segue into my act. There’s such an industry now with event planning that it’s rare you find they don’t have a clue. The worst was doing a show at a seafood restaurant and they’re whacking at their shells during my show. Most of the time, it’s dinner, then comic, then dessert to keep them around.”

“When I first moved to the area in ‘99, I did a show at Caroline’s that Eddie Brill was hosting. He saw me and was very complementary. But, nothing happened. I ran into Eddie occasionally in clubs and he was always very pleasant. But, nothing happened. I figured that he didn’t like me. Then, the summer of 2006, I got an email from Eddie asking if I was free to audition for the Letterman show. It was great. I got a spot right in the middle. It was beautiful. I got the best laughs of the evening. Eddie takes you aside after the show for an exit review. That night he said, ‘You’re going to do the show. Don’t get your hopes up. It might take a while, maybe six months.’ He called in two weeks to say he had a date for me. I didn’t really have time to get too nervous. He took me that week to the clubs. I did a few sets. He’d watch and critique. I cut my time a little bit. Then I went to see the show a few days before mine. Then we did it.”
“From the Green Room, I could vaguely hear him (Eddie Brill) warming up the crowd, whooping them up. I was nervously eating cookies and talking to Elvis (Costello) periodically.”

Some final thoughts – 
on stand-up – “It’s a brilliant art form. To see it done well, nothing makes me happier.”
on why he does it – “I get great satisfaction from crafting a good joke and having them laugh it at.”
on a comic’s effort – “It’s a fundamental thing. People have paid money. Don’t come up with some half-assed premise. At least get it into some sort of joke form. To me, that’s unacceptable.”
on troubled comics – “Maybe they’re musicians but couldn’t play anything. I remember coming up, there were a lot of people who had drug problems who we had to help at times.”
on Rick Springfield – “I have opened for Rick Springfield at the Jersey State Fair. Horrible gig. I didn’t realize it was actually at the fair. About six or seven years ago. It was hot. The 40-year old women stood online for hours waiting to see their precious Rick Springfield. They don’t know there’s going to be an opener. So, the buzz starts, the lights go down, ladies and gentleman (crowd cheers), your comedian this evening (boo). Fortunately, some of these middle aged women felt sorry for me. If it was a Metallica crowd, forget about it.”
on marriage – “Coming up on ten years of being married. Me being more selective is good for the marriage. I can’t be out of the house three weeks out of every month. I’m very encouraged that my January has some high paying gigs where they pick up the travel, and it’s very concentrated; two days here, four days there. So, I’m making more money and spending more time at home. I’m hoping this continues into ‘07. There were many times when I wanted to quit and she said, ‘No, you just need to get in front of the right people.’ She encouraged the move to New York. She’s responsible for my not bailing a long time ago. It’s tough. It can be really demoralizing.”
Speaking of demoralizing, how did Jeff get through that hell gig in our nations’ capital? “I kept calling my wife after each break, telling her I couldn’t keep doing it. But, it was such a big payday, I had to. So, I somehow got through it. They hated me. I hated them. My last task, after it had gotten dark, was to count down from ten for the fireworks. I was supposed to stop at three, then the lights would come down. So, I counted, ‘5-4-3’, then nothing happens. In the distance I hear one guy yell, ‘Go home!’ I had to laugh. Then, the fireworks started. It was awful. Demoralizing, but great pay day.”
To see where Jeff Caldwell is performing, visit his website, standupguy.com