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After his television hit “Everybody Loves Raymond” comes to an end, funny man Ray Romano heads back on the road for an 8-day trip to perform his comedy routines on stage. He travels with his opening act and close friend, Tom Caltabiano, along with an intern from the show, Roger Lay Jr. who’s helping shoot the documentary. They stop in 6 cities from Miami, Florida to Atlanta, Georgia.
Thanks to Ray’s fear of flying, most of the time is spent in the car, taking turns driving from one gig to another, but that’s where you get to see the everyday version of Ray, not the star. There isn’t a lot of time for sightseeing (or anything else) with all the promotional interviews, eating at every opportunity, and waiting on Tom. Ray does take time out for a golf lesson, but then a “mind bet” (that he loses with himself) forces him to give up golf and television in his room for the trip’s duration.
You get to see clips of Ray and Tom doing their stand-up acts on stage, and some hilarious Q&A sessions afterwards. But it’s just as amusing when they’re not doing their stand-up routines - the comedy is unscripted and entertaining, but not as laugh-out-loud funny as TV (there’s no laugh track).
Everywhere he goes people approach him for autographs and photos. He’s
generous with his time, but it’s easy to see how that lifestyle can get
frustrating when you can’t even go down to the pool for a swim or to the
local diner for breakfast in peace. Ray also has to deal with a tornado
warning, driving through the night, an emergency roadside bathroom break,
and a human resources person who’s concerned about one of his risqué
jokes during a corporate meeting where he’s the guest speaker. Life’s tough
at the top.

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