95 Miles to Go 2006

95 Miles to Go originated during a spring break from Everybody Loves Raymond, when Ray Romano embarked on a standup comedy tour across the South. He invited his longtime friend and fellow comedian, Tom Caltabiano, who also served as a writer on Raymond, to be his opening act.

For a decade, Romano and Caltabiano had shared the stage, entertaining audiences together and occasionally recording their adventures on the road. Caltabiano, having meticulously documented their touring experiences since their Catskill beginnings in 1992, persuaded a hesitant Romano to allow filming during their tour. Romano was initially reluctant about having a full-fledged crew trailing them, leading to a compromise where Roger Lay, Jr., an intern from Everybody Loves Raymond and a film student at USC, joined them instead.

This eight-day journey saw them traverse seven cities: Miami, Tampa, Clearwater, Orlando, Jacksonville, Savannah, and Atlanta. The duo flew from Los Angeles to Miami, subsequently renting a car to navigate between the various stops. Over this thousand-mile trek, the cameras captured approximately sixteen hours of footage each day, totaling around one hundred thirty hours across the tour.

Once the tour concluded, an editing bay was set up adjacent to Romano’s office at Warner Bros. Studios—the filming location for Everybody Loves Raymond. The initial cut was an impressive two-and-a-half hours, which premiered to audiences at The Comedy & Magic Club in Hermosa Beach, California. This was followed by fifteen test screenings at theaters across Los Angeles, and a rough cut was showcased at both The Deep Ellum Film Festival in Dallas, Texas, and HBO’s Comedy Festival in Las Vegas. Ultimately, the film reached completion in early 2006 and aired on HBO for an impressive two and a half years.