95 Miles to Go 2006

As the spring hiatus from Everybody Loves Raymond beckoned, Ray Romano embarked on a standup comedy tour of the South, accompanied by his trusted friend and fellow comedian, Tom Caltabiano. This wasn’t just any ordinary tour - it was an opportunity for these two veteran comedians to revisit their roots and bring their unique brand of humor to the people of the region.

As they crisscrossed the country, Romano and Caltabiano’s camaraderie and banter sparked something special, and before long, they were documenting their escapades on film. With a keen eye for storytelling, Caltabiano convinced his hesitant friend to allow their journey to be captured on camera, marking the beginning of an eight-day odyssey that would take them from Miami to Savannah, with stops in Tampa, Clearwater, Orlando, Jacksonville, and Atlanta.

The unlikely duo’s tour was no ordinary comedy routine - it was a chance for these two old friends to reconnect, recharge, and share their humor with a new audience. And so, they set off on the open road, cameras rolling as they navigated the twists and turns of their 1,000-mile journey, capturing over 130 hours of footage in the process.

After the tour wrapped up, an edit bay was set up right next to Romano’s office at Warner Bros. Studios, where Everybody Loves Raymond filmed. The resulting documentary, “95 Miles to Go,” premiered as a two-and-a-half-hour special at The Comedy & Magic Club in Hermosa Beach, California, before being fine-tuned through 15 test screenings at theaters around Los Angeles.

The film made its way to the big screen at festivals like The Deep Ellum Film Festival in Dallas and HBO’s The Comedy Festival in Las Vegas, ultimately finding a home on HBO where it ran for two-and-a-half years.