When Jason Stevens receives word that his great uncle Red has died, his is eager to divvy up the man's massive fortune, but when Jason collects his inheritance he is sent on an unexpected yearlong quest that will lead him to the ultimate gift.

College senior Levi Crowne agrees to escort his great uncle to Loyal, from North Dakota to the Utah retirement home that awaits him, thinking of making a quick buck and getting on with his life as soon as possible. In what becomes a life-changing adventure, however, Levi finds himself transformed by the gentle and wise old man who inspires him to slow down and enjoy the ride.

When eleven-year-old Eddie Dickens's ill parents become "a bit crinkly round the edges," he is taken by his great-uncle and great-aunt, Mad Uncle Jack and Mad Aunt Maude, and embarks on adventures that involve strolling actors, St. Horrid's Home for Grateful Orphans, and a carnival float shaped like a giant cow.

When billionaire Howard "Red" Stevens dies, he leaves the bulk of his fortune to his lazy, ill-mannered grandson, Jason, but in order to receive his wealth, Jason must complete twelve designated tasks intended to make him a better person.