US comedian and Dave Chappelle mentor Tony Woods celebrates 35 years on stage at the Dubai Comedy Festival

The comic says he is continually inspired by being on the road

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It is the kind of shout out that can change a career – even if it turns 35 years old this week.

This is what comic Tony Woods experienced after comedian Dave Chappelle singled him out for praise when accepting the 2019 Mark Twain Prize for American Humour.

Chappelle recalled watching Woods perform in small comedy clubs in Washington DC three decades ago, and finding his career role model.

It was an experience described as similar to jazz maestro Miles Davis seeing his own heroes, the trumpeters Dizzy Gillespie and Donald Byrd in intimate New York venues in the 1940s.

"Tony is my Dizzy and Byrd if I was a Miles," Chappelle said in the ceremony. "You were the first person I ever saw do it absolutely right. You were fearless and told the truth."

A result of the praise is not so much a career resurgence, but a spotlight on a quietly revered figure and more high profile international gigs.

One of which is the 10 day Dubai Comedy Festival, concluding on Saturday.

Woods headlined a string of shows as part of The Comedy Bizarre at the Souk Madinat Jumeirah.

Speaking to The National after a particularly gruelling set on Tuesday, Woods expresses as much delight as discomfort for Chappelle's acknowledgment.

"That shout out was good and bad," he says, with a chuckle.

"Now, the good part is people who never heard of me are now looking at me.”

As for the downside?

"Well, now every little Tom, Dick and Harry is running up to me while I am hanging with my comedian friends and asking me to 'teach them the way'," he says.

"Normally I just say something nice so they can get out of my face but in my mind I am thinking that ‘already you are not worthy to the keys to the palace because you asked for them’.

“That means they are not prepared to go out and put the work in because I am doing that every day.”

The comic is a bandleader

And sometimes those days are harder than others.

While Chappelle may have infused many of Woods’s mannerisms into his own performance, from the anguished yelp and the fake run off a stage after a particular risque joke, the latter’s stream of conscious delivery is a style all his own.

Indeed, Woods approach is akin to jazz musicians: jokes are disassembled, punch lines are sometimes delivered first and anecdotes are told through layers of metaphors and malapropisms.

Such an approach requires a certain mental agility from the crowd.

When on board, the experience is gleefully disorienting. If they are few steps behind, however, as they were on Tuesday, an undeniable edge of frustration seeps through the room.

So what’s one bad night out of a thousands of winning gigs? As it turns out, even the most seasoned pros can find it dispiriting.

"I had a rough sleep after that show," he admits.

"And you know, it's easy to say 'Oh, that crowd is not on my level', but I take full responsibility because I didn't lead them to where I needed them to go.

“A comic is like the guy on the front of the parade, you are meant to follow me and if I don't take you to the destination then that's my bad.”

It also underscores some of the challenges facing comedians today.

More than the financial security coming from steady touring, performing frequently in front of a physical live audience is the only effective way to fine tune material.

The Dubai Comedy Festival is one of the first and biggest gathering of international comics since the pandemic decimated the industry.

It provides the rare chance to perform in a standard club or arena setting after 15 months of shows done mostly on Zoom and eclectic venues such as drive in theatres and airports.

Woods came to appreciate that pre-pandemic diet of steady live performances.

"After all that time off [because of Covid-19], I would get back on stage and I would have a humbling show, but then after that it's just straight fire and I am killing it again," he says.

“But then I am back off the road again and I go through the same process again. It has been a really interesting process but that’s just how it goes at the moment.”

The life of a secret agent

The disruption aside, Woods says there is no other place other than the stage to iron out the kinks of the craft.

It remains the most comfortable space to distil insights and experience of a life and career in motion.

Born in New York, Woods moved to Washington as a 10 year old before making his stand-up debut in the city's Comedy Cafe 35 years ago this week.

After a two year stint from 1989 in the US navy as a medic, Woods went on to build a quixotic comedy career blending mainstream success as part of Def Comedy Jam and P Diddy's Bad Boys of Comedy tours and an appearance in Tiffany Haddish's new Netflix stand-up comedy series They Ready with tours of South-East Asia and Australia.

While he would not turn down out a big television or movie deal, Woods says there are a lot of advantages to a career off the beaten track.

“What I love about stand-up comedy is that you feel a lot like James Bond. You travel the world, go to different cities and meet different people,” he says.

“I don’t like rolling with the same comedians on tour because when that happens you kind of morph into each other and you all sound the same because you experienced the same things and have the same references.

“Like a secret agent, I like go to a new and exotic place, finish my assignment and move on to the next location.”

With Chappelle blowing his cover, the only difference now is the assignments are bigger and better.

Dubai Comedy Festival runs until Saturday, May 22. For details go to