"We blew it"
"Even as it attempts to fashion itself as a timepiece about the hippie generation and its conflicts, the film moves between the language of traditional patriotism founded in the visions provided by "grand national scenery" and a language of revisionism seeking to dismantle traditional notion of Americanism by detailing the nightmarishness of its roads, inhabitants, and modernized landscapes."
The two men sit amid the lull of crickets, Billy with this feet in the sand and a joint on his lips: "We did it, man. We did it, we did it. We're rich, man. We're retirin' in Florida now, mister."
Wyatt: "You know Billy, we blew it."
Spoken bitterly from his lips, Wyatt understands what Billy cannot comprehend: that monetary freedom does not ensure spiritual or social freedom. Wyatt is conscious of the fact that he nor Billy will be accepted into American society because they do not fit the mold. This is evident straight away in the film when the two are turned away at the motel:
Billy: Man, everybody got chicken, that's what happened. Hey, we can't even get into like, a second-rate hotel, I mean, a second-rate motel, you dig? They think we're gonna cut their throat or somethin'. They're scared, man.
George Hanson: They're not scared of you. They're scared of what you represent to 'em.
The men represent a new kind of freedom. Wyatt, ironically nicknamed "Captain America" wears an American flag on his back and helmet. While Billy adorns attire that is seemingly Native American. Both are symbols of American past and present, but paradoxically, the two are ostracized and beat down by the "good ole' boys" (cops, town folk etc.) of conventional American society. At the beginning of the film the scenes cast the road in an "America the beautiful-esque" light, but soon the two encounter the hate, discrimination, and ugliness of the traditionalistic south. Wyatt and Billy are representations of a new wave of thought in 1960's culture, freedom to actually be oneself. I believe that when Wyatt proclaims, "we blew it" he's referring to the "power" of the American dollar, and how after all they'd been though, after how much they'd been torn down and beat up, they were simply going to become everything they hated: two rich white American men living with the upper crust of society. Happiness cannot be bought or borrowed, it has to come from within. And I believe that Wyatt is referring to the disillusionment of this very thought: happiness nor freedom are tangible items, and they certainly aren't for sale.