Kurt Vonnegut's Jailbird follows one Walter Starbuck, the son of a chauffeur who briefly attended Harvard but left to become a soldier in WWII. After a series of unsteady jobs, he becomes Nixon's "advisor for youth affairs." His minor involvement in the Watergate scandal under the Nixon administration left him in a minimum-security prison. The jailer of this prison is one Clyde Carter, who is a distant relative of Jimmy Carter. In jail, Starbuck also meets Kilgore Trout—a character inspired by Vonnegut himself, and featured in his other novels.

When Starbuck is released from jail, his wife has died, and so he goes to New York City in hopes of working as a bartender. While there, he meets former girlfriend Mary O'Looney, who appears to be an impoverished bag lady living under Grand Central Station. She turns out to be the mysterious and unrecognized co-owner of a powerful company, RAMJAC, of which she makes Starbuck vice president. And so, the end of the novel reveals the trajectory of Starbuck's life as one going from rags (as the son of a chauffeur) to riches (at Harvard) to rags (in jail) to riches again.