The Fun-Lan Drive In Theatre opened January 10, 1950. Admission price as 48 cents to see "I was a Male War Bride", starring Ann Sheridan and Cary Grant. The theatre was opened by Carl Floyd and Pete Sones. The single screen theatre had 700 speakers. A bag of popcorn or a small drink sold for 10 cents and hot dogs were 20 cents.

The Fun-Lan had a playground for the children, consisting of swings, merry-go-round, slides and monkey bars. Ira J. Smith was Bobo the Clown. He performed magical tricks and monitored the playground. Later, a train ride was added. The manager, Chuck Rose, and Harry Branan built a railroad station with cross arms. They made a 40' tunnel out of chicken wire and concrete. Employees from the Atlantic Coastline Railroad came to help build the railroad station. Children were charged 10 cents to ride the train twice over the 400' long track which passed by a man-made pond. The train ran seven days a week, one to two hours before the movie started and closed when the show began. In 1963, Harry Branan's children performed trapeze feats and high wire acts Friday and Saturday nights preceding the movie.

The Fun-Lan Swap Shop Flea Market was originally at the Skyway Drive In Theatre in Tampa. It was moved to the Fun-Lan Drive In in 1981. The Flea Market is open 4 days a week, Thursday through Sunday. It is one of the busiest Flea Markets in the Tampa Bay Area.

In 1985, a second movie screen was added. Later, a third movie screen was added, in 2006 a fourth movie screen was added making the Fun-Lan as it stands today.