95 Miles to Go

Ray Romano was initially hesitant about having a full-fledged film crew following him during the tour. To address his concerns, they brought on Roger Lay, Jr., an intern from Everybody Loves Raymond who was also a film student at USC. This compromise allowed Caltabiano's documentation vision while keeping the filming feel more intimate and less intrusive than a professional crew.

Tom Caltabiano had been documenting their touring experiences since 1992, starting from their performances in the Catskills. He was the one who persuaded Romano to allow filming during their tour, seeing the potential in capturing their decade-long comedy journey on the road.

The tour covered seven cities across the Southern United States: Miami, Tampa, Clearwater, Orlando, Jacksonville, Savannah, and Atlanta. They flew from Los Angeles to Miami to start, then rented a car to travel between the remaining stops across this thousand-mile journey.

The cameras recorded approximately sixteen hours of footage each day throughout the eight-day tour. This accumulated to around one hundred thirty hours of content, which was later edited down to a two-and-a-half hour initial cut.

The initial cut, running at two and a half hours, premiered at The Comedy & Magic Club in Hermosa Beach, California. This was before the film underwent fifteen test screenings at theaters across Los Angeles to gather audience feedback.

Romano was reluctant about having a full-fledged crew trailing them during the tour. This hesitation likely stemmed from wanting to maintain a natural, unscripted feel to the journey rather than making it feel like a produced television project, given his already busy schedule filming Everybody Loves Raymond.

His concern about the crew size led to the compromise of bringing on a single film student intern.

Before its final completion, the rough cut was showcased at two festivals: The Deep Ellum Film Festival in Dallas, Texas, and HBO's Comedy Festival in Las Vegas. These festival screenings provided exposure and critical feedback that helped shape the final version of the documentary.

The film reached completion in early 2006 and aired on HBO for an impressive two and a half years. This extended broadcast run provided substantial visibility for the documentary and introduced Ray Romano's comedy tour to a wide television audience.

After the tour concluded, an editing bay was set up adjacent to Romano's office at Warner Bros. Studios, the same location where Everybody Loves Raymond was filmed. The team worked with approximately one hundred thirty hours of footage to create the final documentary, a process that began after the eight-day journey ended.

Tom Caltabiano was Romano's longtime friend and fellow comedian who also served as a writer on Everybody Loves Raymond. The two had shared the stage together for over a decade, performing in the Catskills and touring together before deciding to document their comedy road trip.