Darryl Lenox aimed to revolutionize Canadian comedy

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No one commanded a room like Darryl Lenox. Instead of rattling off one-liners, the baritone-voiced comic would take to the stage and bare his soul, talking about his gradual loss of vision that ended in blindness and thoughts of suicide, among other things. Somehow Mr. Lenox made it funny, chronicling the day the world went dark, and in the next breath, delivering a punchline about mistaking a cab driver for a seat.

“Everything was on purpose,” said Aaron McGeough, co-owner of Heckler’s Comedy Club in Victoria. “He wanted to make a connection, to be philosophical, to be funny and he wanted to do it all as one package.”

Mr. Lenox was an American citizen, but he found an adopted home in Vancouver in the 1990s, and was a fixture at a Tuesday night comedy show hosted by Brent Butt at the Urban Well, where he became a crowd favourite.

“People would stop me on the street and ask if Darryl was going to be doing a spot,” Mr. Butt said in a statement. “He was always there with some advice for younger comics – solicited and unsolicited – he was big into incorporating ‘truth’ into his comedy.”

Indeed, the 6-foot-4-inch comedian’s goal wasn’t just to get belly laughs; he said his aim was to get people laughing “from the soul.” Mr. Lenox wanted to be the greatest comic in the world, and even more, he wanted to revolutionize Canadian comedy.

Those plans were cut short. On April 16, he died at Vancouver General Hospital after suffering an aortic dissection four days earlier. He was 57.

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The comic’s career spanned 34 years and included appearances on Conan O’Brien’s show Conan, Black Entertainment Television’s Comic View, A&E’s An Evening at the Improv and Comedy Central’s Jamie Foxx’s Laffapalooza. He won the Seattle International Comedy Competition in 1999 and headlined regularly in both the U.S. and Canada. In 2012, his stand-up special Blind Ambition was picked up by Starz network and Stage Time Magazine named it one of the top five comedy albums of the year.

“You could not say no to this man – and trust me, I tried,” said Lou Viola, Mr. Lenox’s friend and U.S. manager. “He made you want to work for him because he was uplifting to be around. He made you feel good.”

Darryl O’Flynn Lenox was born in Las Vegas on Jan. 28, 1966, to Emma (née Smith) and Clarence Lenox. Clarence was in the Air Force when the couple met, and served in Vietnam.

After his parents separated, his mother married Charles Woods. Darryl, who was the second eldest of five children and the only boy, described his childhood home as a matriarchy. The family moved to California where Ms. Woods worked as a telephone operator and Mr. Woods worked at Sears. He was the store’s first Black manager. He was a laid-back man who passed on his love of chess to Darryl and coached his Little League team.

As a child, Darryl was nearsighted and wore thick glasses that he often lost or broke, much to his mother’s frustration. Despite his poor eyesight, his sisters say he was a talented athlete who was obsessed with sports. “He would just eat, breathe basketball when he was little,” his sister Tony said. “His childhood dream was to go to the NBA.”

He adored his sisters and was fiercely proud of them. But living in a home full of women began to chafe at him. He felt the men in his household lived in the corners while the women dictated the plans. He yearned to know his biological father. He moved to Seattle when he turned 18 and found a drastically different man than the one who raised him. The senior Mr. Lenox was working as a pimp and drug dealer in Beacon Hill.

In Seattle he had his first taste of comedy at an open mic night at the Comedy Underground. Mr. Lenox got up on stage and unleashed his whole life story. The audience loved it. He later told his sister Erin that he had performed his set with his eyes half-closed.

That was it. He knew: “This is the only thing I’m going to do for the rest of my life,” he said.

A believer in astrology (he was an Aquarius), Mr. Lenox knew the universe had a plan and he believed in the power of affirmation and manifestation – sometimes to his detriment. For example, trying to manifest a big agent by claiming he had already been signed landed him in trouble both with the Seattle comedy circuit and his first wife. Their marriage lasted just four months and he found himself with nowhere to go but Canada.

The Comedy Cave in Surrey, B.C., booked him for a week in 1994, and Mr. Lenox took the opportunity to start over. He liked how genuine Canadians were and, while a lot of his jokes about race didn’t land the way they did in the U.S., he quickly adapted his material.

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Mr. Lenox met his second wife, Clair Reilly-Roe, when she was waiting tables at the Urban Well. A young musician from Ottawa, she was captivated by his stage presence and struck by his positivity. “He loved people, he loved their stories, he spent time and he listened,” Ms. Reilly-Roe said. “Man, they would tell him everything in two seconds of meeting him.”

His care for others extended to his fellow comedians, including another regular at the Urban Well, 13-year-old Seth Rogen. In Mr. Rogen’s 2021 memoir, Year Book, he credits Mr. Lenox with giving him the advice he needed to write Superbad: Write what you know (Mr. Lenox would go on to narrate the recollection in the audio version of Mr. Rogen’s book).

A career breakthrough for Mr. Lenox came in 2010 with the show that would become his special, Blind Ambition. It was filmed at Vancouver’s Vogue Theatre. Ms. Reilly-Roe says the couple produced it themselves, raising the funds from friends and with inheritance money from her grandmother. Three years later, Mr. Lenox told Marc Maron on his WTF podcast, “It was the first time that I ever felt like this is what I’m supposed to be doing.”

For a few years, he was on top of his game, and then things took a turn when Mr. Lenox experienced a series of hard knocks. His first wife died by suicide, his father was diagnosed with cancer and his marriage to Ms. Reilly-Roe came to an end, just short of their 10th anniversary.

Mr. Lenox lost sight in his left eye in 1997 after suffering multiple traumas including a detached retina. His right eye, he joked, was like the single mother who worked so hard she was run ragged. He became allergic to his glaucoma medication in 2018 and his field of vision in that eye was limited. Although a surgery in Vancouver restored his sight for a few years, by 2020, he was blind.

But Mr. Lenox was nothing if not an optimist. He knew something beautiful would grow out of the pain. His third act was off to a strong start. He had founded an entertainment company called Ellison Rains. His 2021 album Super Bloom was well-received, and then, last summer, he was interviewed by writer Kiese Laymon for an episode of National Public Radio’s This American Life.

The appearance sparked interest from a publisher and Mr. Lenox coaxed his former manager, Mr. Viola, out of retirement to help him cement a book deal. He signed with United Talent Agency and by the time he died, Mr. Lenox was working in earnest on a proposal with pop culture writer Caseen Gaines.

There were other plans too – he was booked to headline at Halifax Comedy Fest and Winnipeg Comedy Festival. And he was doggedly pursuing a dream to buy national comedy club chain Yuk Yuks from its CEO and founder, Mark Breslin. Mr. Lenox took him out for lunch in Toronto years ago and said he wanted to buy the chain, Mr. Breslin recalled. “I said, ‘Darryl, I doubt you can afford it.’”

That didn’t deter Mr. Lenox. He devoted himself to trying to make the numbers work. He had a vision to reinject life into comedy clubs, produce more digital content and improve things for comics.

“He wanted to change the industry,” comedian and long-time friend Ron Vaudry said. “He wanted to take over the Yuk Yuks circuit in Canada and expand through the States and build a new comedy empire – reconstitute it in a stronger and more artistic way.”

Tasked with notifying Mr. Lenox’s loved ones of his death, Suzanne Stewart, Mr. Lenox’s executive assistant and friend, had her work cut out for her. Mr. Lenox had friends from Vancouver to New York, Tampa Bay and Milwaukee. His death stunned the comedy community.

“I’m going to miss him,” Mr. Butt said. “The comedy scene is going to miss him.”

Comedians who can be insightful and uplifting are a real rarity, Mr. Viola said. “The best stand-up comics pulled up a big mirror,” he said. “And Darryl had the ability for just about everybody to be reflected back by a large, sightless African-American man.”

“But he saw us and he made us see ourselves in his comedy.”

Mr. Lenox leaves his parents; his sisters, Tony Robinson, Nychele Thomas and twins Erika Wilson and Erin Woods; his nieces and nephews and countless friends.