The tagline for this is "Who's scamming who," and the answer is Warner Bros. and whoever parts with nine bucks and 89 minutes of their life.
Based on an early Elmore Leonard novel, The Big Bounce presumably refers to the thrill you get from committing crimes. In this case, though, it refers to what happens when you doze off and your head falls into the seat in front of you. Not only does this wannabe comedy-crime caper take on the languorous pace of the Hawaiian tropics, it never manages to create a single interesting character nor clever plot twist.
Owen Wilson is Jack Ryan, a petty criminal and drifter, who gets roped into a scheme by Nancy Hayes (Sara Foster) to rip off her sugar daddy, hotel magnate Ray Ritchie (Gary Sinise). Along the way, he gets adopted by judge and resort owner Walter Crewes. There are also appearances by Charlie Sheen, Willie Nelson, Harry Dean Stanton and Bebe "Lilith" Neuwirth as Alison Ritchie. (I assume everyone signed on to have a working vacation in Hawaii.)
We're supposed to see Sinise as the villain because he's legally building a hotel on land he bought, but which a small group of Hawaiians—the only natives you'll see in the film, and naturally all wearing muumuus and grass skirts—want undeveloped. Walter is a good hotel owner, presumably because his is falling apart. We're also supposed to see Wilson as being clever because ... well, just because.
Jack and Nancy are angling for $200,000 of Ray's, which he needs to pay some muscle to move the protesters along. (That motive reminded me of Austin Powers' Dr. Evil initially demanding a paltry $1 million in exchange for the world's safety; I guess $200,000 bought a lot more in 1969.) Walter is in there, too, conspiring with Alison to kill Ray for his estate ... which is all in Alison's name. Nancy also is in on that plot ... but doesn't want a share.
And so it goes, with a predictable and dully written romance developing between Jack and Nancy, Ray disappearing for most of the film, and Freeman's character uttering left-over maxims from Shawshank. Hey, but at least Stanton does a memorable turn.