Synopsis: "95 Miles to Go" came about during a spring hiatus from "Everybody Loves Raymond" when Ray Romano did a standup comedy tour of the South. He brought along fellow standup comedian, former roommate, and Raymond writer Tom Caltabiano as his opening act. Romano and Caltabiano had been performing standup together for ten years and had periodically videotaped their time on the road. Caltabiano, who had been documenting their road tours since their first one in the Catskills in 1992, convinced a reluctant Romano to allow a tour to be filmed.

Romano did not want a full crew traveling with them, so they compromised and had Roger Lay, Jr., an intern from "Everybody Loves Raymond" who was also a USC film student, accompany them. The eight-day tour took them to seven cities: Miami, Tampa, Clearwater, Orlando, Jacksonville, Savannah and Atlanta. They flew from Los Angeles to Miami, then rented a car and drove to each city. During the thousand-mile road trip, the cameras rolled approximately sixteen hours a day, ultimately capturing one hundred thirty hours of footage.

After the tour ended, an edit bay was set up next to Romano's office at Warner Bros. Studios, where "Everybody Loves Raymond" filmed. Initially a two and a half hour version was shown to the public at The Comedy & Magic Club in Hermosa Beach, California. That was followed by fifteen test screenings at theaters around Los Angeles. A rough cut was shown at The Deep Ellum Film Festival in Dallas, Texas and HBO's The Comedy Festival, Las Vegas. The film was completed in early 2006.