Jackson is about two homeless men in Los Angeles, Donald and Sam. At the start of the day Donald is given a $20 bill (also known as a "Jackson"). The film follows the two and shows their adventures throughout the day with this money, and features songs from various operas.
Barry Primus as Donald
Charlie Robinson as Sam
Steve Guttenberg as Businessman
Debra Jo Rupp as Nice Lady
"Una furtiva lagrima from Donizetti's Elixer of Love – Richard Brown and Shawnette Sulker
"Champagne Aria" from Mozart's Don Giovanni – Cedric Trenton Berry
"Habanera" from Bizet's Carmen – Elaa Lee Romani/ Chorus: Ariella Vaccarino, Aleta Braxton, Pilar Diaz, Tahlia McCollum
Sextet from Donizetti's Lucia di Lammermoor – Jennifer Suess, William Gorton, Michael Sokol, Fred Winthrop, Benjamin Von Atrops, Leberta Clark; Music performed by Remy Zero
Monologue by Ibn Hakia from Tchaikovsky's Iolanta – John R. Jackson
"O mio babbino caro" from Puccini's Gianni Schicchi – Gustavo Hernandez Jr.
"Va, pensiero" from Verdi's Nabucco – Socialists: Clamma Dale, Kimarie Torre, Lauren Lee
Chorus: Laura Decher, Frances Garcia, Erin Neff, Sara MacBride, Gregory Stapp, Antoine Garth, Gary Murphy, Tom Oberjat, Raphaela Rose Primus
"Love Cannot Be" (written by J.F. Lawton)
"El Pueblo" – George Lawton and John Cross
"Vamos a la Fiesta" – Julie Griffin
"Abrabo" – Way Depp, Robidebs Okyeame, Paa Dogo and Brekete
"I Wish I Was in Dixie Land" – John B.J. Smith
"Downtown Birthday" (written by J.F. Lawton)
Jackson was filmed mainly in Los Angeles with the exception of one scene shot in Kentucky.