When his rich granddad, Howard "Red" Stevens (portrayed by James Garner) died, Jason (Drew Fuller) thought he was going to inherit a piece of the old man's multi-billion dollar estate, but it came with a condition. In order to get his share of the willed inheritance, Jason must complete 12 separate assignments within a year. Each assignment is centered around a "gift". Gifts of Work, money, friends and learning are among the dozen that Jason must perform before he is eligible for the mysterious "Ultimate Gift" his grandfather's will has for him. Throughout his trials and tribulations, the family attorney, Mr. Hamilton (Bill Cobbs), and his secretary Miss Hastings (Lee Meriwether) attempt to guide Jason along the path his grandfather wishes him to travel. However, the problem they have is that Jason has lived leisurely using his grandfather's money as an under-achiever who has never had to genuinely work, and who believes through a young adulthood of loneliness that money is the only pathway to making life decent. For instance, to carry out the first task he has to fly to Texas, and naturally assumes he has a first-class seat, and is annoyed when he discovers he has a coach class seat, complaining to the steward "Don't you know who I am?"
On his return after completing the first task in Texas, everything he values is suddenly taken away from him - luxury apartment, his restored muscle car (a 1970 Dodge Coronet R/T) and money - and he is left homeless. His trendy girlfriend, Caitlin (Mircea Monroe), ditches him when his credit card is rejected at a fancy restaurant and she is mortified when he asks her if she could pay the bill. After his mother (Donna Cherry) tells her son she cannot give him help as part of the agreement, Jason miserably finds himself being ejected from private property he wishes to rest on, and wanders the city for the first time truly alone.
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