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Lee H. Tillman’s comedy is a lot like a woodwind.
His cashmere setups rise and fall like legato notes from a clarinet, his words forming a carefully chosen melody that vaguely resembles the syrupy run of a bassoon, and his punch lines land much like a flute punctuates a musical phrase. This analogy feels particularly apt given that Tillman’s debut comedy special, Bad at Math (available on YouTube), was performed with the accompaniment of a jazz ensemble. As the band noodled melodies and rhythms behind him, Tillman expertly wove his jokes into the jam.
“When I decided to do a special, I just wanted to have some type of musical aspect to it,” Tillman, 45, explains. “I’d been to New York and met a guy who plays drums for this YouTube channel where he’d jam with people—usually another musician, sometimes a singer, but one time he asked me, and it was awesome. That’s why I got the band. It’s because I always think it’s important to be funny—I believe I’m funny—but it’s also important to be original and have something that no one else is doing.”
Though his medium is comedy, Tillman’s punch lines seem to occupy the same space as your favorite rapper’s flow. His pace is relaxed, his demeanor loose and languid, and his delivery rhythmic and pointed. It’s a vibe clearly influenced by jazz and hip-hop alike.
“When I originally started doing comedy, I just emulated what I thought comedy was supposed to look like,” Tillman says of his early days in the craft. “I was trying to tell longer stories and just be more boisterous, but it wasn’t working. I’m not as dry as I am onstage—that’s me to the comedic degree. When I was trying to tell stories, I wasn’t getting to the punch line, and a lot of times I would just rant. So I was like, I’m gonna write setups and punch lines. That’s when I started realizing more of my voice.”
Despite Tillman’s steadfast presence in Portland’s comedy scene, his arrival here is only semi-recent. “I actually started doing comedy in L.A.,” Tillman says. “And L.A. is just a really tough place to start. After maybe four or five years, I just kind of quit.”
Fortunately for Portland, the pandemic forced Tillman into what has since become a rather familiar career and life recalibration. “I think everyone had this moment where we were like, OK, this all can go away at any moment. What do you really want to do? What is it that you want to do?” Tillman recalls. “And I was like, well, I want to try comedy again because I think I can really do this.”
There’s a universal appeal to Tillman’s joke-telling style. The structure of his sets is straightforward, and his influences are apparent and arguably timeless. “I grew up in the ’90s, where you would just watch whatever was on Comedy Central, from Tim Allen and Jeff Foxworthy to Martin Lawrence and Katt Williams,” Tillman explains. “If someone had a comedy special in the ’90s, I saw it. No matter who it was, I soaked up everything. People like Patton Oswalt, Bob and David, Dana Gould, Sarah Silverman—just that era of comedy. But if you’re talking about my style as far as what I do, I feel like I’m more influenced by rappers than I am by comedians. My favorite rapper right now is Boldy James but also Vince Staples. I think Pusha T is an incredible writer.”
This revelation is why comparing Tillman’s comedic style to an instrument common to jazz compositions feels so fitting. “What I do is setup/punch line, which is like a punch line rapper—like a battle rapper where everything has to hit. When they’re in the circle and make the crowd go, ‘Oh my God!’—that’s a laugh to me. So that’s the reaction I’m trying to get every time.”
Thankfully, fans concerned about losing Tillman to a larger market can put their worries to rest. “I really want to show off Portland. I want people who come through to know that we have some really great comics here,” Tillman says. “I’m more interested in winning over the people of Portland because a lot of times I’ll tell people that I’m a comic, and they don’t know that we have shows. They don’t know that there are comics producing shows. But when some big comic comes around, they go and see them. My goal is to build a bigger scene here so that other comics passing through from San Francisco on their way to Seattle will say, ‘We need to go to Portland because they’ve got good crowds there.’ And we do have good crowds. I want that for our local comics too.”
What is the funniest thing Lee H. Tillman has seen in Portland? How local efforts to “keep Portland weird” fall short: “A lot of people talk about how weird Portland is, but I’ve lived a lot of places and, like, it’s not. I don’t really think about how it’s weird or funny or anything. It’s just people, man, just people.”