Jerry's Drive-In originally opened as Jerry's Barbecue in 1939 by Jerry Glass. Located at 2815 E. Cervantes Street, Jerry's underwent change and a new owner in February 1952. A Richmond, Indiana native, Ray "Gramps" Wessel bought the business and changed the name to Jerry's Drive-In. Ray, now the forefront of the Jerry's name, appealed to the customers dressed in his standard white button-up shirt and red tie.

The small diner serves simple Southern cuisine and includes breakfast, lunch, and dinner. Items on the menu are reasonably priced and range from grits and hash browns to fried chicken gizzards, hamburgers, and a variety of seafood.

In May 1999, the restaurant caught fire and destroyed everything from the black and white floor tiles to the old-fashioned barstools and some of the wall memorabilia. It took approximately $200,000 to rebuild the restaurant and it was only out of business for two months. While the restaurant was out of commission, a handful of staff and the owners operated with a limited menu in a single-stove concession stand in the back parking lot.

Wessel believes the reason for his success is his and his son's ability to remember their customers' names. The restaurant was so popular, it also served as the location for many dates and proposals for young couples. The restaurant is now owned by Jimmy and Pam Halstead and managed by Sharon Johnson, the granddaughter of Wessel. It still remains a Pensacola landmark today and is the place to go for a bacon cheeseburger.