Chicago comedy 2023

The Best Chicago Comedy Albums & Specials to Watch (So Far) This Year

Last year, independent comedy stand-up specials and albums began to appear in droves. 

An online renaissance motivated more artists to take risks. Years ago, comedians would have to wait for a huge platform to produce comedy specials. With the intense drive as of late, many stand-ups have chosen to forgo waiting for such opportunities.

The pandemic affected everyone differently, but stand-up comedy seemed to grow from it.

Many comedians who had performed live for decades, suddenly found themselves holed up with nothing but time and ideas. This formative period brought the community some of the most powerful and necessary comedy since 9/11. When the country is in shambles, comedians are the unwilling voice of society.

While 2020 was the blueprint and 2021 was the warmup, 2022 was the execution. 

The mecca of comedy, Chicago put out some of the best work in the country. From comedians you are sure to see on HBO, Netflix, and Showtime, here are some of the top names you should know and the voices you must listen to.

Best Chicago Comedy Albums and Specials In 2023 (So Far)

CALVIN EVANS X B.O.R.N

Chicago Comedy Specials Calvin Evans x  B.O.R.N.

Evans performs | Sourced from Facebook

Calvin Evans is the man. 

At the time of taping his debut album, he already had a stunning resume. In the first few years of his career, he was crowned Chicago’s Next Big Comic; in the later half, he was one of eight finalists in NBC’s Stand-Up competition. He has starred on several shows in the past decade: a recurring role on Southside, with notable appearances on Shameless, Chicago PD, Sherman’s Showcase, APB, and Hart of the City. If you are ever fortunate enough to catch him live, he is usually the show’s unforgettable headliner. 

Calvin is great at being unforgettable. 

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Usually, comedians that are Evans’ caliber tend to have multiple recorded projects. So, why did it take him twelve years to tape an album? He just didn’t want to. In fact, Evans said he never had any intentions of taping one. 

“When the offer came – I figured why not?” 

Helium Records approached him to produce an album. Evans saw it as an opportunity; he wanted to make an introduction to both himself and his brand of comedy. B.O.R.N showcases Calvin’s observational philosophy and brilliant delivery. While Jeremy Essig produced and engineered, Evans’ brought his best. 

The album is a must-listen debut project. Listening to him at work is nearly like music, save for the laughs in between. His style of comedy is several steps ahead; on B.O.R.N, he purposely uses cerebral jokes to paint images for listeners. The premises serve as the track listing and give the audience insight into his esoteric mind. 

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Covid Changed Me, You Should Get Tested, The Trump Years are not only gold, but spotlights his poignant view of the pandemic. 

Calvin taped in Philly, which is far removed from his stomping grounds of Chicago. He liked it that way. He compared being there to an away game but felt he received honest responses to his set. The album was taped over two shows; the first crowd was predominantly white and the last was mostly black. Fortunately, Evans has no trouble connecting with any demographic. 

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The performance is played intimately, with jokes being presented within the confines of a private conversation – there’s breaks for laughing, brief interaction, and real time observations.

“Thanks to all the people who booked me for shows and gave me chances and opportunities to cultivate my comedy over the last 12yrs. They are co producers of this album.

Calvin Evans
The artwork.

Calvin is masterful as he presents the work he has been crafting for over a decade; it is thought-provoking, hilarious, and necessary all at once. Check out B.O.R.N on all platforms.

Ontonio Kareem x See Y’all in 30

Photo credit: Ashley NiCole Lane

Ontonio Kareem is a swiss-army knife. 

The Chicago born artist is multi-faceted; he is an MMA competitor, Ford model, actor, musician and stand-up comedian. A man of many talents, Ontonio has perfected communicating through every available medium. He’s appeared in modeling campaigns, quietly dropped a music project, guest starred on Chicago Fire, and produced one of Chicago’s hottest shows for the last few years. 

Ontonio’s comedy is different. It’s relaxed, dazed, and gut-wrenchingly funny. His punchlines sneak up on you through a unique deep, drawl. The well-written material and delivery got him far; Just six months into his stand-up career, he did his first showcase at Laugh Factory. After winning a competition through Verified Laughs, he moved rapidly through the comedy scene while skirting checkpoints. He has toured with notable names, such as SNL’s Chris Redd and Abbott Elementary’s Janelle James

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After producing shows and becoming a bonafide headliner, Kareem decided to release his own special. 

Ontonio was motivated by the complacency that surrounded him. While most comedians take close to a decade to tape a special — it took him just four. He had deep concerns about his career flying by and he would have nothing to show for it. Akin to ending up in the winner’s circle without highlights or having your arm raised with no championship around your waist. 

Kareem looks at stand-up as any other art form; how musicians’ discography changes over time and represents their world at the time. With See Y’all in 30, Ontonio leaves a love letter to this version of himself, all the growth he has done – and still has yet to do. The stunningly intimate special was taped at The Hideout in Chicago. 

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Felonious Munk (For Life, ABC) hosted, a man Ontonio cites as a “wizard” for his ability to control and entertain  a crowd. Skyler Higley (CONAN, The Onion) opened for Kareem; he is called the “consistent killer” for his record of dominating a room time and time again. With two star comedians just as powerful as he is, Kareem’s taping could not have been more perfect – except his parents witnessing their son “act a damn fool on stage for the first time.”

What Ontonio calls “acting a fool” is far different from the presentation of the special. We get to instead witness a man bearing his soul; he is unafraid to let the world see him put the pieces together. Kareem doesn’t believe in waiting for the perfect moment or decade to share your art, he is in love with the process. 

Check out See Y’all in 30.

Vik Pandya x No Refunds

Photo courtesy of Pandya

Vik Pandya is a workhorse. 

You would be hard pressed to find a stand-up comedian that works harder. If you have been in Chicago at all in 2022, you would see his face on a poster somewhere. It was his year, really. Vik has always been a high achieving comic, with a laundry list of accomplishments.

His talent and drive have opened doors for him; he has featured in seventeen comedy festivals and opened for the likes of Roy Wood Jr. While he has been a go-to fixture for his reliability and business sense, Vik decided to build a room. 

With all the time spent on stage, he ended up crafting some of his best work. While most comedians take years to formulate one special, Vik filmed three. His first, No Refunds, was taped in April but released in August by Dry Bar Comedy – the clean version of Netflix. Pandya speaks of being extremely thoughtful when selecting his material, as Dry Bar Comedy has a large audience. 

“I wanted it to be an introduction of me to folks who likely had never heard of me or my style of comedy. I viewed it as an opportunity to showcase for potential new fans, with hopes of attracting them to my other content.”

Vik Pandya

Vik taped two separate sets on the same night in Provo, Utah.  Though he is one of the best stand-up comedians in Chicago, even he faced a challenge; Pandya was actually super sick the night of filming. Fortunately, he had a ton of support.

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The staff at the theater even went to pick up medicine for him. It clearly helped a lot – no one, except for Vik, could even tell he was sick. The material and delivery were on point, despite weathering a sinus infection. 

No Refunds received a wave of attention, acclaim and positive feedback when Dry Bar released clips. It is definitely a carefully thought out and crafted introduction to Vik Pandya. It is worth checking out.

Obi Ehn x 30 at The Den

Ehn’s headshot | photo credit: Gabriel Alvizo

Obi Ehn is enigmatic. 

Chicago comedians may not agree on much, but they agree that Obi is massively talented. He is hilarious, frenzied, wise, and feverish on stage. His voice into a microphone is almost as magnetic as his looks. One look at Ehn’s Instagram gives you an overview; his luminescent photos showcase a man that turned down a future in modeling in favor of creation. 

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He is in his own colorful box; not only does he do stand-up, he is a writer, director, poet, and musician. Ehn’s resume includes a win for Best Independent Comedy Pilot. The project, Where Are You Going?, was co-written with fellow comedian Vishnu Akella. The Pilot appeared on Paramount Plus. He is also a great musician with an EP titled Severance Package

He dances through multiple mediums to communicate his inexplicable messages; his favorite, at least now, is stand-up. Though we could be here to break down everything he has created, we’re here for his 30 minute special taped at The Den Theatre. 

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“Thirty at The Den” is a wild ride. Obi’s style of comedy is in line with his self presentation, a poetic black boy with alot on his mind. The exact definition of an enigma is “a person or a thing that is difficult to understand, mysterious, or puzzling.” While it happens to describe him perfectly, being enigmatic is beneficial in the world of comedy. 

When asked why he chose to tape a special this year, the answer was simple; he bought a jacket he really liked off Instagram.  

“I’ve been performing for 6 years now — I was ready to shed that material and those ideas. The goal was to honor that growth.”

Obi is like a butterfly in this “self titled mixtape,” as he deemed it. It’s transformative, touching, and hilarious. He allows himself to be goofy, free, and thought-provoking. If it’s not apparent that he is one of the best things brewing in comedy, it will be by the conclusion. 

While Ehn refused to nail down what he hopes people take away from it, one thing is for sure; to mention anymore to you would do you a disservice. 

Please watch 30 at The Den. Now

Incoming & To Be Released Soon

Adam Burke x Weaponized Empathy

Burke performs at Paper Machete | photo credit: Sarah Larson

Adam Burke is striking.

The only entry on this list with a Wikipedia page, Burke is a highly decorated – and respected – comedian. With nearly two decades of experience, Burke has accomplished quite a bit. He has been profiled several times and acclaimed for his intelligent brand of comedy; Adam is notable for always having something to say. 

He was voted Chicago Reader’s Best Stand-Up in 2014 and placed first in Second City’s Up Next competition. He created two webcomics, is a regular panelist on NPR’s Wait Wait…Don’t Tell Me!, and currently hosts the YouTube original The 5 O’Clock Somewhere News with Comedian Adam Burke

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Adam has become a go-to for Emmy winners such as John Oliver, John Mulaney and Oscar Nominees such as Kumail Nanjiani. So it’s no surprise that his special is absolutely killer. It’s everything that specials should be made of: care, distinctness, brilliance, and finesse. Produced by A Special Thing Records, who recorded his debut album,  Burke brings his finest. 

I think I just kept waiting until I had the “perfect hour” and I realized I had been waiting for ten years.

Adam Burke

He speaks with a unique accent as he was born in Australia and raised in Northern Ireland. 

Sometimes, this can enhance the punchlines Burke sneaks in. His charisma drips through his range of unique jokes; most of his material remains high brow with silly undertones covering everything from society, culture, and history. Adam believes most of our values to be silly and arbitrary – something he has no trouble conveying.

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Taped in Chicago at The Newport Theater, Adam Burke’s album is a perfect project. Over two shows, Chicago favorite Lele Mason hosted; Sean Flannery, Chelsea Hood, and Sonal Aggarwal were the supporting acts leading into Burke’s phenomenal album taping. 

Coming from the man hailed as a lot of comedians’ favorite comedian, you would be remiss to not give it a listen…once it drops. Make sure you follow Burke to stay posted.

Joe Kilgallon x Good Grief

Kilgallon headlines Comedians You Should Know | photo credit: Rodescu Hopkins

Joe Kilgallon is profound. 

The proud Chicago boy has been one of the most respected, hilarious, and in-demand comedians for a while now. Kilgallon’s recent move to Los Angeles has continued his good fortune; he became one of the quickest comedians to get passed at Hollywood’s world famous Laugh Factory and is one of the founders of the critically acclaimed Comedians You Should Know.

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In addition to appearing on NBC and TBS, he parlayed his love of sports into the popular podcast Comedians Talking Sports. 

As an opener for the likes Roy Wood Jr and Steve Byrne, he continues to be one of the craft’s best. Kilgallon shares his straightforward, powerful, and hard-hitting style of comedy with the world. While his career continues to be prosperous, Joe’s personal life was hit by tragedy; last year, his father unexpectedly passed away.

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The loss was felt hard — he and his father were extremely close. Being the great artist and son he is, he knew he wanted to have a tribute in his next special. This one is aptly named Good Grief. 

“I wanted people who had gone through grief to know that it is okay and that the focus should be on the positive and how lucky we were to have that person in our lives.”

The special was taped in New York City, even though Kilgallon is proudly “Chicago ‘til I die.” Doing it away from home gave him a good measure on his material. He even called it a fun challenge. 

With the first show being standing room only — and having familiar faces — Joe created some incredible moments by weaving in improv. Reports from the taping call it one of Kilgallon’s finest performances packed with surprises and award caliber writing. One thing that is guaranteed is lots of laughs centered around grief and vulnerability. As this is personal to him, it seems like Joe has put his world on tape. 

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As a man intent on leaving a legacy of greatness, he succeeds in multiples at offering us an honest portrait; Joe Kilgallon is a man who loves three things: comedy, sports, and above all, his family. 

Follow him to listen to Good Grief as soon as it drops.

Kendale Hamlett x Drunken Night Out

Hamlett performs at a sold out show | photo credit: Shane Anthony

Kendale Hamlett is esteemed. 

The Washington born comedian is a natural talent. He is an anchor in many states’ biggest comedy clubs and a frequent opener for Emmy-Nominee Nimesh Patel. Kendale starred in the documentary “Step into Stand-Up” and featured in numerous festivals including the historic Just For Laughs.  Oh, he is also the creator and producer of the award-winning podcast Drunken Night Out

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The revered, smooth, and highly charismatic comedy veteran has defeated all the roadblocks. Adversity is not foreign to him; He has parlayed years of suffering from alcoholism into something great. Hamlett runs a highly successful touring comedy show that shares its name with his podcast, My Drunken Night Out. The show works like this: comics tell a drunken story, then get drunk forreal, perform, then get drunker and do crowd-work. It’s a wild ride.

While this show is incredible in its own right, it takes a great comedian to conceive it. 

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It also takes a little bit of pain. Some would say it is fitting that Kendale shares a last name with the Shakespeare work, Hamlet. One of the central messages in Hamlet is “in life, you will be able to get away with something for long, but not forever.” The theme applies directly to him grappling with his drinking problem. 

He stated that he felt he got “really good at” alcoholism last year. However, being the warrior he is, he overcame it. For his special, he did Drunken Night Out as a solo show and subbed the alcohol; He got really, really high instead. 

“I was literally like Goku in ultra instinct form, nothing was throwing me off; I was just going with everything and had some great laughs.”

The project is remarkable and full of many distinctions. It is animated and part of a new series incoming from a collaboration with his wife, Lauren. Kendale shares his most personal material yet in his special. He is beyond his A-game and backed by his family, who helped produce it. His twin brother is director of photography and has worked for prominent film companies; his wife served as the incredible animator. 

With a new style of stand-up presentation, impactful material, masterful comedian, and a lot of heart – Drunken Night Out is something you can not miss. Watch out for the drop here.

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