Top stand-up comedian Bert Kreischer and World War II US Army “Buffalo Soldier” Roy J. Caldwood will be featured during parade festivities on Saturday, January 27.

Tampa, Fla. (January 16, 2024) – Tampa Bay native and top stand-up comedian Bert Kreischer will serve as Grand Marshal for the 2024 Seminole Hard Rock Gasparilla Pirate Fest on Saturday, January 27. Today’s announcement by Ye Mystic Krewe of Gasparilla, Seminole Hard Rock Hotel & Casino Tampa, and EventFest, also introduced World War II US Army “Buffalo Soldier” Roy J. Caldwood as this year’s honorary Community Hero. 

The 2024 Seminole Hard Rock Gasparilla Pirate Fest, scheduled for Saturday, January 27, in Tampa, will feature the Gasparilla Invasion and Parade of the Pirates presented by Ye Mystic Krewe of Gasparilla and the Gasparilla Pirate Fest Street Festival presented by Bud Light and 101 N. Meridian Apartment Homes.

“There’s no better person who embodies the pirate culture and a love of Tampa than the one and only Bert Kreischer. What a delight to have Bert serve as the 2024 Seminole Hard Rock Gasparilla Pirate Fest Grand Marshal!” said Ye Mystic Krewe of Gasparilla Captain Truett Gardner. “All I have to say is look out Tampa Bay! We look forward to Bert’s energy and hometown pride to lead this year’s festivities for a lively crowd along Bayshore Boulevard.”

Bert Kreischer, once dubbed Rolling Stone’s “Number One Partier in the Nation,” is a 2023 Pollstar top-grossing stand-up comic, JUST FOR LAUGHS Stand Up Comedian of the Year, and the star of a recent major motion picture, “The Machine.” Razzle Dazzle, his 5th stand-up special, has charted in the top 5 stand-up specials on Netflix and has been accompanied by at least one of his other three specials in the top 20 since its debut. He returns to his hometown of Tampa after his recent sold-out show at AMALIE Arena, hailed as “one of the best storytellers of his generation, seamlessly and sincerely sharing anecdotes about his family and fatherhood while proving that there’s a way to take his [party-boy] antics into middle age.” In addition to his stand-up, Kreischer is also a prolific podcaster and the creator and host of the popular YouTube cooking show Something’s Burning, which has racked up over 25 million views on the platform. Kreischer founded Berty Boy Productions, the production home for his video and podcast projects and the Fully Loaded Comedy brand, and is currently on the Tops Off World Tour.

Beginning at 2 p.m., Kreischer and Caldwood will lead more than 115 parade floats, 53 krewes, seven marching bands, and the infamous Ye Mystic Krewe of Gasparilla pirates down a four-and-a-half-mile parade route along Tampa’s famed Bayshore Boulevard. 

2024 Community Hero Roy J. Caldwood is a World War II US Army “Buffalo Soldier” who served in the 92nd Infantry Division Reconnaissance Troop 2nd Platoon. He became a medic during the war in the 92nd Infantry Division, the only Black Infantry Division in WWII deployed for combat in Europe. He earned a Bronze Star for his heroic actions when he volunteered to remain in a village under eminent German attack to aid a sick Italian man. After the war, Caldwood pursued a career with the New York City Department of Corrections, where he worked for over 21 years as an Assistant Deputy Warden and Program Director at Rikers Island. He received multiple awards, including the New York City Commissioner’s Award for Bravery in 2001 and the New York City Department of Correction Guardian Association Medal of Honor, Valor & Merit in 2016. Now 101 years old and a proud Tampa Bay resident, Caldwood is an author, a community justice advocate, a proud member of Grace Episcopal Church Tampa, and an honorary member of the Buffalo Soldiers & Troopers Motorcycle Club of Tampa. 

“Mr. Roy Caldwood’s bravery and compassion is the definition of a community hero,” said Steve Bonner, President of Seminole Hard Rock Hotel & Casino Tampa. “His belief that there is good in all human beings and his desire to make a positive impact should be an inspiration to all of us. Even at 101, Mr. Caldwood continues to serve as a community justice advocate and share his learnings with as many people as possible. We’re grateful for the opportunity to recognize his longstanding service and history in our community and worldwide.” 

Reserved tickets are still available for the Seminole Hard Rock Gasparilla Pirate Fest. To purchase, visit You can also follow the Gasparilla revelry on social media @GasparillaTampa. 

Tampa’s signature community events, the Ashley Children’s Gasparilla presented by Chick-fil-A Tampa Bay and Seminole Hard Rock Gasparilla Pirate Fest, are marketed, managed, and produced annually by EventFest, Inc.

Rounding out this year’s honorees is Chick-fil-A Tampa Bay Community Hero, Pete Alonso. A Tampa native, Alonso was a star at the University of Florida, memorably clubbing the longest home run in College World Series history, before quickly ascending through the minor leagues and achieving his dream of making the big league roster during the 2019 Spring Training season. The Plant High School alum is now a three-time All-Star first baseman for the New York Mets, winning Rookie of the Year (2019) and Major League Baseball’s Home Run Derby twice. In 2020, he and his wife, Haley, founded The Alonso Foundation, which creates a positive and lasting impact in the New York and Tampa Bay communities by supporting youth causes, providing aid for veterans, and promoting animal welfare.