Almost A Wiseguy is the gritty life-story of Vince Ciacci, a hair stylist, with ambitions to become a made-man in the Mafia. But his alcohol and drug abuse kept that from happening. Ciacci grows up without the love and acceptance he needs from his parents and seeks that from the wrong type of people. It isn't until the birth of his daughter, his only child, that he realizes the destructive nature of his life. In an effort to stop his downward spiral, he reluctantly seeks and finds help in AA, but his road to recovery isn't an easy one, with many starts and setbacks.

One year after the assassination of President John F. Kennedy, the Vietnam War continues to escalate and the draft hangs over the heads of young men in Corona, New York. The sounds of doo-wop, the Four Seasons, Elvis, and Sinatra still play on the jukebox at Al's Bar and Grill where twenty-one year old Frankie Russo and his friends hang out. On one of the most important days in young Frankie's life, he has an accident with his brand new 1964 Pontiac Bonneville and it becomes one of the worst days of his life. The actions he takes following the accident change his life forever.