Flamingo Comedy Fest Brings a Week of Laughs to South Florida

The message from Benjamin Leis, cofounder of Comic Cure, is simple and straightforward.

“There hasn’t been a big comedy festival in South Florida in a long time," he says. "We’re about to change that.”

Beginning this Friday, he and his brother Richy will once again deliver laughs to our corner of the world — as their company has done since 2015 — but now on a much more ambitious scale.

The Flamingo Comedy Festival is a weeklong affair offering a variety of shows, many of them free, in and around Boca Raton. Dana Eagle, Phil Hanley, and Miami’s own Dave Barry will headline the seven-day fest, which will also feature entertaining and informative daily events, some geared toward audience participation — and not the heckling kind either.

For example, Monday, Richy Leis will host and instruct a free stand-up comedy class at the Flamingo House, a space built for creatives who need somewhere to work and brainstorm. Tuesday, the Dubliner will be home to the Trivia Challenge, hosted by Wilma McAwesome, a longtime trivia master who’s toured the improv circuits for years.

For anyone who wants simply to sit back and laugh, the inaugural edition of the Flamingo Comedy Festival kicks off strong with a trio of veterans.

Dana Eagle is a bipolar, Jewish lesbian who specializes in self-deprecating humor and the occasional Mitch Hedberg/Steven Wright absurdist puns and non sequiturs. She’s perfect, actually. Eagle is dark, loopy, quirky, and funny.

The author of the tongue-in-cheek How to Be Depressed: A Guide, Eagle has appeared on NBC's Last Comic Standing, The Late Late Show, Comedy Central, and Comics Unleashed, and several times over the years, she’s performed as part of USO tours for American soldiers.

Eagle will be very busy this weekend: She’ll appear twice at the fest, first Friday night to discuss her book, and then she’ll close out Saturday night after 16 local comics take the stage at the Boca Raton Innovation Campus to compete for Florida's Funniest Female 2019.

Standup comedian Phil Hanley is less self-deprecating and more self-loathing, but with a hint of cockiness.

Hanley, who appeared on The Tonight Show Starring Jimmy Fallon earlier this year, recently released the comedy album Please Don’t Chit-Chat While I’m Pursuing My Dream.

The Vancouver native is a regular at the famous Comedy Cellar in New York City and has also appeared on Late Night With Seth Meyers, The Late Late Show, The Pete Holmes Show, and John Oliver's New York Stand-Up Show on Comedy Central.

Hanley is set to close the festival next Friday, October 25, as the headliner of United We Stand-Up, a show benefiting local veterans and disability service organizations. Comics from the U.S. Armed Forces will also perform.

The award-winning author, columnist, and humorist Dave Barry for years was a central voice in South Florida as a Miami Herald columnist, assessing the local scene and its relation to the culture and climate of the nation.

Barry will appear at the Downtown Boca Raton Public Library for an event to discuss his latest book, A Field Guide to the Jewish People, released last month. Unsurprisingly, the free event is sold out. Barry, no doubt, would be the first to see the humor in that fact.

Flamingo Comedy Festival. Friday, October 18, through Friday, October 25. Information and events calendar via eventbrite.com.

Dana Eagle. 2 to 3 p.m. Friday, October 18, at Faulk Center for Counseling, 22455 Boca Rio Rd., Boca Raton. Tickets are free with registration via eventbrite.com.