May Comedy Picks

Jesus Trejo. Photo from jesustrejo.com.

With the COVID-19 pandemic (hopefully) waning and live entertainment returning, there’s never been a better time to try and get out for a laugh. The previously packed small, intimate rooms that host the world’s best headliners are thankfully filling back up, and you don’t wanna miss out in the month of May. There are some true “killers” (relex, it’s an industry term) coming through Jacksonville, so be sure to peruse some of our finest, hand-picked selections.

5.12-5.14

Ari Shaffir at Comedy Zone

Known for his take-no-prisoners approach, frenetic to deadpan delivery and cutting punchlines, Ari Shaffir continues to prove to be one of the more controversial but consistently hilarious voices in contemporary comedy. The “Skeptic Tank” podcast host has also gone on quite a spiritual journey, even adopting yoga and traveling the world regularly separate from comedy, with neither dulling his timing or edge. Be sure to catch a set and prepare to be battered in the most delightfully entertaining way possible.
$25-$30. 7:30 & 10 p.m. 3130 Hartley Rd., Jacksonville, FL; comedyzone.com // @comedyzonejax

 

5.19-5.21

Jesus Trejo at Comedy Zone

The modern stand-up scene has no shortage. Between his Showtime special “Stay At Home Son,” along with a regular roles on Netflix’s “Mr. Inglesias,” Freeform’s “Alone Together” and TV Land’s “Teachers,” the Long Beach native and Comedy Store regular continues to stay booked and busy. $20. 7:30 & 10 p.m. 3130 Hartley Rd., Jacksonville, FL; comedyzone.com // @comedyzonejax

5.21

Chris Kattan & Friends (Allie Goodwich & Surfer Jesus) at High Dive Gainesville

There’s an entire generation of comedy fans to everyday citizens who will instantaneously recognize references like “Mango,” Mr. Peepers, and “The Roxbury Guys,” all thanks to the immensely talented physical humor of Chris Kattan. With stints on CBS’ Celebrity Big Brother, ABC’s The Celebrity Dating Game, he has also published an autobiography, “Baby Don’t Hurt Me,” which details the incredible highs and lows of his time at SNL, and its aftermath (including sustaining a life-altering neck injury). For the insights and anecdotes alone, definitely worth a visit. $25-$35. 8 p.m. 210 SW 2nd Ave, Gainesville, FL; highdivegainesville.com // @highdivegville

Wild ‘N Out at VyStar Veterans Arena

While he’s gone on to be a multi-hyphenate singer, actor, radio and television host, Nick Cannon began his journey in comedy, as a breakout member of the original cast of Nickelodeon’s “All That.” This began a natural evolution to another blockbuster comedic commodity: “Wild ‘N Out,” the popular MTV improv series that has been running since 2008. The live show will prove no different, with teams of talented comedians competing head to head in lightning-fast rounds, that include rap battles, stand-up, special guest performances. Along with dancers, special guests and maybe even the chance to become part of the fun. $55. 8 p.m. 300 A Philip Randolph Blvd., Jacksonville, FL; vystarveteransarena.com // @vystarvetarena

5.29

No Cap Comedy Tour

Industry veteran Deray Davis (FX’s “Snowfall, Fox’s “Empire,” “21 Jump Street”) combines forces with  clearly talented headliners like Lil Duval (“Meet The Blacks,” “Scary Movie 5”) and Michael Blackson (“Coming 2 America,” “Next Friday”), along with up and comers DC Youngfly, Chico Bean, Karlous Miller, B Simone and Black Ron. $60. 7:30 p.m. 300 A Philip Randolph Blvd., Jacksonville, FL; vystarveteransarena.com // @vystarvetarena

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