Raised in a working class Jersey neighborhood, Weissler started his first theater troupe in the 1960s with little in the way of money or experience. He met Fran Weller—then a married mother of two and ten years his senior—when she filled in one day at the box office of a theater where he was performing; they were married a year and a half later. The Weisslers struggled to make ends meet for a number of years, traveling up and down the East Coast with their troupe and performing Shakespearean dramas. In 1982, they made their first trip to Broadway with an Othelol</em revival starring Christopher Plummer and James Earl Jones.
The Weisslers put on an occasional Shakespeare play over the following years, but mostly turned their attention to the campier pastures of musical revivals, staging productions of Gypsy, Fiddler on the Roof, and My Fair Lady in the late '80s and early '90s. A 1994 iteration of Grease!, opening with Rosie O' Donnell as Rizzo, proved a major crowd-pleaser, lasting for over 1,500 performances at the Eugene O'Neill Theatre. But the couple scored their biggest hit with 1996's Chicago. The show won seven Tonys, including Best Actress for Bebe Neuwirth.
Since the success of Chicago, the Weisslers have produceda number ofe other musicals with mixed results, including a well-received revival of Annie Get Your Gun with Bernadette Peters; 2000's Seussical, in which Rosie O'Donnell agreed to take over the role of the Cat in the Hat in a last-ditch effort to boost ticket sales; 2003's Kathleen Marshall-directed revival of Leonard Bernstein's Wonderful Town; and 2005's tepidly-received Sweet Charity, with Christina Applegate in the lead role. Increasingly, the Weisslers have turned to stunt casting to lure audiences to their productions. Melanie Griffith, Usher, Huey Lewis, Kevin Richardson and Ashlee Simpson have all been recruited for roles in Chicago, and Brooke Shields was brought in to take on the lead role in Wonderful Town nine months into its run.