Tampa Bay’s best comedy gigs this week, including Healing with Humor fundraiser, Kill Tony and more

Healing With Humor, a non-profit founded by local comedian (and previous Best of the Bay winner) Rahn Hortman, raises funds for individuals and their families impacted by sickle cell disease. The comedy show is the second such fundraiser for the organization held at Side Splitters, with the first netting around $6,000. 

Hortman knows how the disease can affect a family personally: Two of his adult children suffer from it, with one recently released from the hospital after a lengthy stay. A portion of ticket sales will go to the charity, as will proceeds from a raffle and a 50/50 drawing. Local business leaders Michael Donor and Erica Paradise are also personally sponsoring the event. 

In addition to Hortman, the lineup includes another Best of the Bay alum (Johnny B), Jenn Weeks, and headliner Mark Gregory, who has appeared on Fox, Aspire, the Just For Laughs Comedy Festival and the Apollo Theater.

Get info on this gig below, plus more of the best comedy coming to Tampa Bay May 7-20. And check out our comedy venues guide for more.

LeMaire Lee Thursday, May 7. 8 p.m. $23.80. Side Splitters, Tampa 

Nurse’s Night Out with Greg Williams Thursday, May 7. 7:30 p.m. $22.50. Snappers, Palm Harbor

Kellen Erskine Thursday, May 7. 8:30 p.m. $23.58. Clearwater Comedy Club, Clearwater

Damn Gina! With Finesse Mitchell and Tisha Campbell Thursday-Saturday, May 7-9. 7 p.m. Thursday; 7:30 p.m. Friday; 6:30 p.m. and 9:15 p.m. Saturday. $30 and up. Funny Bone, Ybor City

Insight with Chris Van Vliet Friday, May 8. 4 p.m. $42 and up. Funny Bone, Ybor City

Heroes Off Duty Comedy Tour Friday, May 8. 7:30 p.m. $44.25 and up. Capitol Theatre, Clearwater 

Leah Bonnema Friday, May 8. 8 p.m. $20. Greenlight Lounge and Kitchen, St. Petersburg

Tyler Fischer Friday-Saturday, May 8-9. 7:30 p.m. and 10 p.m. Friday; 8 p.m. and 10:30 p.m. Saturday. $30 and up. Side Splitters, Tampa

Stand Up & Storytelling with Chris Kael, Craig Gass, and Riki Rachtman. Friday-Saturday, May 8-9. 7 p.m. and 9:30 p.m. Friday; 6 p.m. and 8:30 p.m. Saturday. $28 and up. Side Splitters, Wesley Chapel

Michael Mack Friday-Saturday, May 8-9. 7 p.m. and 9:30 p.m. $22.50. Snappers, Palm Harbor

Jimmy Kopteros Friday-Saturday, May 8-9. 8:30 p.m. $23.58. Sunshine City Comedy Club, St. Pete Beach

Chris Robinson Friday-Saturday, May 8-9. 8:30 p.m. $23.58. Clearwater Comedy Club, Clearwater

Healing with Humor featuring Mark Gregory, Johnny B and Rahn Hortman Saturday, May 9. 5:30 p.m. $28 and up. Side Splitters, Tampa

Ginger Kelly, Tara Zimmerman and Kathy McSteen Saturday, May 9. 6:30 p.m. $20. Beef O’ Brady’s, Parrish

Kill Tony Saturday, May 9. 7 p.m. & 9 p.m. $51.30 & up. Mahaffey Theater, St. Petersburg

Landon Bryant (LandonTalks) Sunday, May 10. 6 p.m. $30 and up. Side Splitters, Tampa

Mother’s Day Unfiltered with Jimmy Kopteros and Ginger Kelly. Sunday, May 10. 7 p.m. $22.50. Snappers, Palm Harbor

BC Murphy Wednesday and Saturday, May 13 and 16. 8 p.m. Wednesday; 8 p.m. and 9:30 p.m. Saturday. $20. Coconuts, St. Pete Beach

Queen and King of Reality Show with Nene Leakes and Carlos King. Thursday, May 14. 7 p.m. $37. Funny Bone, Tampa

Marcus Monroe Thursday, May 14. 7:30 p.m. $22.50. Snappers, Palm Harbor

Zach Rushing Thursday-Saturday, May 14-16. 7 p.m. Thursday; 7 p.m. and 9:30 p.m. Friday; 5:30 p.m. and 8 p.m. Saturday. $41 and up. Side Splitters, Tampa

Learnmore Jonasi Thursday-Saturday, May 14-16. 7:30 p.m. Thursday; 7 p.m. and 9:30 p.m. Friday; 7 p.m. and 9:30 p.m. Saturday. $28.80. Side Splitters, Wesley Chapel

Radel Ortiz Friday-Saturday, May 15-16. 7 p.m. and 9:45 p.m. Friday; 6:30 p.m. and 9:15 p.m. Saturday. $32 and up. Funny Bone, Ybor City

Tom Briscoe Friday-Saturday, May 15-16. 7 p.m. and 9:30 p.m. $22.50. Snappers, Palm Harbor

Drew Davis Friday-Saturday, May 15-16. 8:30 p.m. $23.58. Sunshine City Comedy Club, St. Pete Beach

Jeff Klein Friday-Saturday, May 15-16. 8:30 p.m. $23.58. Clearwater Comedy Club, Clearwater

Jessica Michelle Singleton Sunday, May 17. 6:30 p.m. $28.80. Side Splitters, Tampa

Christian Johnson Sunday, May 17. 6 p.m. $27 and up. Funny Bone, Ybor City

Bill Pettifer, Caroline Post and Lauren Dufault Sunday, May 17. 7 p.m. $15.38. Motorworks, Bradenton

Sierra Layko and Sean Harper Monday, May 18. 8 p.m. $15. The Beach Theatre, St. Pete Beach

Te Davis Wednesday, May 20. 8 p.m. $20. Coconuts, St. Pete Beach

---

Pitch in to help make the Tampa Bay Journalism Project a success.

Subscribe to Creative Loafing newsletters.

Follow us: Google News | NewsBreak | Reddit | Instagram | Facebook | BlueSky

---

This article appears in May 07 – 13, 2026.