What Would Jimmy Do? Music and Lyrics, Bo Calloway ©2025. All Rights Reserved.
Bo grew up with the windows down on family road trips along Florida’s legendary A1A — from Key Largo to Key West — soaking in the turquoise water, salty breeze, and Jimmy Buffett’s carefree anthems. Those summers planted the seeds for his storytelling: a blend of country roots and tropical soul.
“What Would Jimmy Do?” is Bo’s homage to those childhood memories and to the man whose music defined them. The song is a laid-back but heartfelt reflection — when life gets too heavy, deadlines press too hard, or the boss is barking too loud, Bo leans back and asks the question we all know the answer to: what would Jimmy do?
With steel-drum sounds and an easy island groove, this song captures both the escapism of Buffett’s world and the very real pull of the Florida Keys. It’s about hammocks instead of boardrooms, sunsets instead of stoplights, margaritas instead of routine.
The release on August 30th, Florida’s official “Jimmy Buffett Day,” is no coincidence. Just as the state honors Buffett’s cultural contributions and environmental efforts, Bo releases this single as a toast to the lifestyle, the music, and the Margaritaville spirit that inspired him from the start.
“What Would Jimmy Do?” isn’t just a song — it’s a reminder, a philosophy, and a compass pointing south down A1A.