Pennsylvania, 1956. Frank Sheeran, a war veteran of Irish origin who works as a truck driver, accidentally meets mobster Russell Bufalino. Once Frank becomes his trusted man, Bufalino sends him to Chicago with the task of helping Jimmy Hoffa, a powerful union leader related to organized crime, with whom Frank will maintain a close friendship for nearly twenty years.
In the wake of their friends' marriages and eventual offspring, longtime pals Julie and Jason decide to have a child together without becoming a couple. By becoming "time-share" parents, they reason, they can experience the joys of parenthood without significantly curbing their personal freedom. However, when Julie and Jason both become involved with others, they discover that they secretly harbor romantic feelings for each other.
A washed-up '80s pop star gets a chance at a comeback when reigning pop diva Cora Corman invites him to write & record a duet with her, but there's a problem--Alex hasn't written a song in years; he's never written lyrics and he has to come up with a hit in a matter of days.