On September 12, 2005 in Hollywood, California, Vince Vaughn took the stage at the Music Box Theater in Hollywood, California and began a comedy tour featuring four stand-up comedians. In the spirit of the old west variety shows, Vaughn played host to the ensemble of comedians and performed improvisational sketches with surprise celebrity and musical guests.

The film chronicles the journey of Vaughn and the comedians as travel over 6,000 miles and perform 30 shows in 30 consecutive nights in cities across the nation. Through on-stage performances and behind-the-scenes interviews, the grass roots documentary breaks down each comedian's life-altering experiences and the personal and professional challenges that unite four comics, one movie star and fans from Hollywood to the Heartland.