WILMINGTON — Cliff Cash has traveled more than 700,000 miles in the last decade building a standup career.
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Come November, his work will culminate in a special to be recorded by local production company Lighthouse Films. Cash’s goal is to pitch it to streamers.
“Netflix is certainly my first choice,” he said, “but HBO or Showtime, I mean, yeah. Lighthouse definitely has all those relationships.”
The 42-year-old — originally from Gastonia but has lived in Wilmington his adult life — released a 2021 comedy album, “Half Way There,” on Stand Up! Records, which charted No. 1 on iTunes. It consisted of material from a show he did at Dead Crow Comedy Room, where Cash has performed often. He credits its founder Timmy Sherrill for always being supportive, as well as local comedians, family and friends.
Among them is Billy Mellon, local restaurateur of manna, bar owner of Earnest Money & Sons and Greenfield Lake Yacht Club, and entrepreneur of music venue Bourgie Nights. Mellon is producing Cash’s Thalian Hall special, “The Long Road.”
The comedian has performed at Bourgie Nights numerous times over the last few years to sell-out crowds. During one of the shows, Mellon said he took a break from running a dinner shift at manna to catch Cash’s set.
“I expected to stick around for a few minutes, get bored and go back to working at the restaurant,” Mellon told Port City Daily. “However, the show didn’t get 30 seconds in and I was dying laughing.”
Mellon said the hysterics continued after a few more times catching Cash’s act.
“His delivery is so matter-of-fact,” Mellon continued. “He’s smart and he uses it well in his bits.”
Mellon stepped in to help once he learned a year ago that Cash was considering moving on from the industry. The constant travel — Cash has been to 48 states — was wearing on him. With age, a new relationship and being a caretaker for a parent, Cash was contemplating going back into real estate, a profession he had been involved with before taking on life as a career standup.
“That ‘midlife crisis’ we all go through,” Mellon recalled.
Cash pinpoints himself “naive” going into the business. He thought putting sweat equity in, with boots on the ground, would get him to where he wanted to be.
“I thought, if I’m the funniest in this town or that town, or on this show or that show, eventually, stuff’s gonna start falling in my lap,” he said. “Nothing falls in your lap, especially in America — unless your daddy puts it there.”
But standup is another beast. There are highs and lows, sometimes performing for a crowd of 1,400, other days a crowd of two.
“It kind of took me a couple years of other people believing in me before I really believed in myself enough to think I could really go for it,” Cash said. “I think comedy is like life in the sense that all the really good and really bad days stand out. The ones that were pretty good run together. I’ve definitely had more good than bad, but I’ve had some tough crowds.”
Cash said when he started out in the business, he was acutely aware of the “many paths” someone could take to make it in standup. Being at the right place at the right time with a person of interest taking notice topped the list, but usually it comes with moving to New York or Los Angeles. Cash is a Southern boy with a love for nature at heart.
He said making a one-off viral video of a show or incident that grabs attention of late-night show hosts often is the modern way of being discovered.
“All of a sudden, you’re an overnight sensation, and you can play any club you want,” Cash said. “I don’t think that’s going to happen for me; I’m not a viral video kind of guy.”
Instead, Cash forged his own path.
‘Every chance feels important because it could be your break’
The comedian’s journey started in 2011.
His first night on stage consisted of opening for local comedian and Dead Crow Comedy Room founder Timmy Sherill. It was outside of Charleston in Summerville, South Carolina.
“I think it went pretty well for a guy who was new to standup,” he said. “Now that I’ve been a professional touring comic for several years, I look back and it’s kind of hard to say how good or bad it was. Sometimes I’m glad I don’t have videos of all my early gigs. I’m sure if I saw videos of all my early gigs, I may cringe at some points.”
Since, he’s performed on a greater scale to audiences of a couple thousand. Pre-Covid he was hosting upward of 300 shows 10 months out of the year. He hits the road in an upfitted vehicle as his “homestead” and has been through multiple wheels in a decade: a diesel Mercedes, a wagon, a Sprinter van.
“I’ve also toured in a bunch of cars in between when something would break down or get worn out,” Cash said. “I toured the whole West Coast in a tiny Ford Fiesta.”
He has camped at 45 of the nation’s 65 national parks and picked up a love for nature photography along the way. He also sells his prints while touring.
After wrapping shows in the Pacific Northwest, he camped at Mt. Rainier National Park during July Fourth and enjoyed a cheeseburger and beer at the foot of a mountain town near the park. He was biting into his burger as fireworks popped and crackled overhead.
“Maybe the most American I’ve ever felt,” Cash said.
He camped at Pinnacle National Park before doing the San Luis Opispo Festival, where he was voted “Best of the Fest.” The park was a six-and-half hour drive from where Cash was performing in L.A. and once he arrived, he slept in his car on a rural road nearby.
“This is when I was really hustling to see all the national parks,” he said. “[Pinnacle] was a new national park at the time and there wasn’t a campground there yet.”
A nine-hour hike turned into 14 due to the comedian getting lost, but he managed to get back to his vehicle as the sun was setting, before hitting the road for three hours to make it to the SLO Festival. He performed to sold-out crowds that weekend with the bill of other comedians.
Cash has opened for multiple acts, up-and-comers and veterans alike, such as Kevin Nealon, Nate Bargatze, Bert Kreischer, Dave Attell, and “The Daily Show” comics Ronny Chieng and Wyatt Cenac. Not to mention he’s made friends with promoters and bookers.
“It’s a really good feeling knowing I have this network of good people all around the U.S.,” he said. “It gives you the feeling that you can’t fail.”
He also has been part of Comedy Central’s “Up Next” in Boston performing to more than a thousand people in the Wilbur Theater. Cash said that show stands out as one of his “best sets” so far.
“Every one of those chances feels important because you know that it could be your break, it could lead to something bigger, it could be the thing that makes your life a little easier,” he said. “Then there’s the realization, maybe by the end of the night or maybe by the end of that week, that whatever the chance was, it didn’t happen. Those lows are as intense as the highs. I’ve definitely learned not to overly invest emotionally in any one thing.”
Much of his act consists of impersonations of characters that feel relatable to many Southern folks — “our uncles, our neighbors, that asshole on the road,” Mellon said. Cash tackles the stereotypes others put on the South and he doesn’t shy away from politics or current events ticking the headlines. He’s been known to punch up (Trump) to those in power and avoids punching down to marginalized voices (LGBTQ rights).
“A lot of people in the country have these strong opinions about what America is, what it should be,” Cash said. “And most of the people yelling those opinions the loudest have never seen the country.”
Some of the comedian’s favorite moments on the road have come offstage: watching a sunrise with someone from China who didn’t speak English or with an elder from New Zealand, also a photographer.
“I’ve seen how multicultural we are — it’s the best thing about our country,” Cash said.
Yet, these days Cash said he’s taking a different approach that can keep an audience laughing on both sides of the aisle. The goal is to not alienate anyone.
“If you can kind of dance around the minefield of triggering words, you can get away with saying a lot more and the same thing without upsetting people,” he said. “I talk a lot about racism and homophobia, for example, and if you do that in a way without using certain words, it makes it hard for somebody to talk back. Nobody’s going to stand up and go, ‘Wait just a minute, buddy. I’m a racist, and I don’t appreciate you making fun of racists.’”
He homes in on the prevalence of double standards and hypocrisy. While some topics may seem heavy for comedy, Cash said finding the levity is the end-goal. He prepares often by having inner dialogue and even running it across friends and family in normal conversation to see what lands.
“What I’m doing is shining a magnifying lens on the absurdity of these sort of small-minded worldviews,” he said. “Like if this whole group of people makes fun of one old guy for falling off a bicycle — well, he’s an old guy riding a bike, and he rides his bike every day, which is pretty impressive. Whereas this other guy probably couldn’t get on a bike if he tried and is lying about winning golf tournaments. You know him: the alpha male — not scared of anything, except for trans teenagers and Mexicans and Muslims. It kind of writes itself. And I think if you do it in a way that’s not too mean, you can make it funny without pissing anybody off too much.”
But, really, he also hopes to make audiences think.
The hustle
Cash has been his own agent and manager since day one. It’s something he sees continuing. He said most industry reps aren’t approaching standup comics until they’ve “made it.”
“Nobody’s coming along and saying, ‘Hey, I think you’re the funniest person, so I’m going to help you,’” he said. “It’s more like, ‘Hey, you’re doing well, you need an agent; let me have 15% of what you’ve already busted your ass doing.’ … It seems a little opportunistic.”
The grind hasn’t been an easy one. When Covid-19 hit, Cash lost shows and his primary income. Rather than turning to livestreaming, he began doing smaller house sets. This also meant confronting a fear: fewer faces in the crowd.
“For most comedians, the smaller crowds are usually the hardest,” he said.
It rings true for Cash as well. Performing for less people has been the least favorite and most laborious part of the job, he said. However, the pandemic helped him overcome it. He embarked on roughly 80 private house shows, often with only 20 people.
“It’s made me a better comic and I feel like I’ve never been more on top of my game,” Cash said.
The smallest crowd he performed to so far was in Florida, for two couples in a hotel banquet room that normally held 100 people.
“That night I gave myself a mental pep talk and decided right then that it didn’t matter,” he said. “I set my mind to just have a good time on stage and make sure those two couples had a really good time. They laughed the whole show and both bought a CD afterward.”
Life nowadays is somewhat back to normal, with venues he performs in also evolving. Over the last year-and-a-half, Cash has begun booking shows on cruise ships. He has traveled to the Bahamas and across multiple places in Mexico. Cash is headed to Cozumel later this month and from there flies to Portugal to load onto another ship. Attendance has been solid, bringing in upward of 600 people a night.
While grateful to travel internationally, he still has a love for the club circuit.
“You might play a club that seats 300 people, and there might only be 100 people there, but those 100 people are really glad they came and now they really like your comedy,” he said. Whereas on cruise ships, “they just came because karaoke was full. But it’s still really nice to have big, full rooms on the ships.”
Cash’s new material centers on some of those experiences, as well as life in a new relationship, and of course the litany of hot topics surrounding political headlines, such as the Jan. 6 insurrection.
Performing in historic Thalian Hall, however, is a dream. He envisions the special will lean into his worldwide travels and have local appeal. Wilmington comedians Wills Maxwell and Drew Harrison will open the show, and Cash’s brother, New York Times-bestselling author, Wiley Cash, will emcee the event.
Music will be featured by local performing artist Sean Thomas Gerard scoring the intro and outro, with insight into Cash’s journey included. Cash envisions the special showing him camping in his van with the sun on the horizon. He then packs it up and prepares to perform in front of more than 500 people in Thalian Hall.
“Then the camera is going to follow me from the van into the venue and onto the stage,” he said, where he’ll do an hour set.
In the lobby will be an exhibit of Cash’s photos for sale as well.
“I just really want to honor the fact that this community believed in me enough to come to all my shows starting out, which kind of gave me the faith in myself to take the next step,” he said. “That amount of support has been really crucial to me achieving the modest success that I have.”
Cash has given back to the community in return. Often, his local shows act as fundraisers: as coat drives or to gather blankets and gloves for unsheltered individuals. He has produced gigs that help with refugee resettlement camps and even did political fundraisers for progressive candidates.
He said Mellon’s assistance to make “The Long Road” come to fruition has been integral; the entrepreneur fostered the meeting with Lighthouse Films. Mellon said it’s because he believes in the comedian.
“When I tell people about Cliff, I reminisce about the first time I saw him,” he said. “I tell them, ‘If you want to laugh to the point of almost running out of air, come see Cliff.’ I watch a lot of comedy shows and I have a few that I really think are great at what they do: Bargatze, Bill Burr, [Dave] Chapelle, [Anthony] Jezelnik, and Cliff’s as funny as any of them — period.”
All the funds from ticket sales will go to Lighthouse for filming the show, according to Cash. The company just completed a project with Kevin Hart and has worked with large corporations, such as Michelin, Nissan, Chase Bank and Capital One.
There is a VIP ticket ($165), which includes a meet-and-greet with the comedians and Cash’s brother, Wiley. Hors d’oeuvres and drinks will be served. It also includes admission to an afterparty a few blocks away at Bourgie Nights, with live music from Sean Thomas Gerard.
Tickets otherwise are $45 and available here. The show takes place Nov. 9, 7 p.m., at Thalian Hall.
“I had no idea at the time how hard the road would be or how long it would take to really build up to the point of making a decent living,” Cash said. “That’s why I’m calling this special ‘The Long Road.’ It definitely has been. It’s been fun but it hasn’t always been easy.”
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