Pirate Jean Laffite helps Andrew Jackson defeat the British during the War of 1812, Sam Zemurray becomes a banana kingpin and Louis Armstrong becomes a jazz legend.
| Name | Type | Role | |
|---|---|---|---|
| Derek Waters | Writer | ||
| Daryl Johnson | Guest Star | ||
| Jason Momoa | Guest Star | ||
| Miles Brown | Guest Star | ||
| Rudy Mancuso | Guest Star | ||
| Andre Royo | Guest Star | ||
| Gloria Calderón Kellett | Guest Star | ||
| Maestro Harrell | Guest Star | ||
| Craig Anstett | Guest Star | ||
| Jack McBrayer | Guest Star | ||
| Allan McLeod | Guest Star | ||
| Ben Covette | Guest Star | ||
| Thomas Middleditch | Guest Star | ||
| Derek Waters | Director |