In 1939, the building on the corner of Dixie Highway and Flamingo Drive housed an ice cream parlor and coin laundry. It was that year that it was bought by Elias Chalhub and opened up a bowling alley across the hall, the Carefree Bowlaway, with wooden pins and 10 lanes that were the largest in the state at the time. “Pin boys” were used when it first opened who would manually set the pins and roll the balls back to the players until automatic pin setters were later installed.
In 1948, the move theater opened with “The Egg and I” starring Caludette Colbert and Fred MacMurray. It originally had 800 seats but the two front rows were removed for a curved stage constructed in front of the screen, reducing the seating to 772. Facing the street was retail space with offices and a dressing room located above it.
In 1960s, the theater was managed by General Cinemas and throughout the 70s and early-80s, it had become a second-run bargain house.
In 1984, the Carefree was bought by John Stoll, who was the founder and president of Fantasma Productions, one of the world’s longest standing and largest concert promoters and producers. From 1986 to 2001, he operated the Comedy Corner where the bowling alley was located along with a retail art gallery.
At that time, it was one of the top venues for comedy in the nation. “Larry the Cable Guy” Dan Whitney got his start at the Comedy Corner as the warmup act. Some other well-known entertainers who performed there included Jerry Seinfeld, Chris Rock, Bill Hicks, Bill Mayer, Steve Harvey, Norm MacDonald, Drew Carey, Pauly Shore, and “Carrot Top” Scott Thompson.
Live concerts were also played here which included musical acts by Weird Al, Brian Setzer, Meat Loaf, and many more. BB King would also play there once a year to sold out crowds.
Stoll began offering second-run movies, and The Rocky Horror Picture Show which ran continuously for more than 15 years. In the 90s, first-run foreign and art films were shown, making it the most successful art house in the nation. The theatre became host to the Palm Beach Film Festival and South Florida Jewish Film Festival every year.
On December 6, 2005, the theater and Chinese restaurant who they shared the building with were evacuated when the roof collapsed over an empty storefront. This prompted officials to close the building.
In 2016, it was announced that the property was purchased by real estate developer Charles S. Cohen, who plans on building a complex which will include a six-screen theater and 94 luxury apartments, in two buildings in a 1920’s Mediterranean style similar to that of The Breakers hotel. Demolition of the Carefree Theater occurred on September 7, 2016.