Eugene Martone (Macchio) is a student of classical music at Julliard's, with a side interest in studying the blues, and a fascination with the legend of Robert Johnson.
After learning about the potential of a "lost song", Eugene tracks down bluesman Willie Brown at a minimum security hospital. Willie Brown is less-than-amused at Eugene's shallow fascination with the blues, but offers the song to him if he Eugene breaks him out of prison and helps him get to Mississippi.
Together, the two take a journey where Eugene learns about what true blues is, and how legends are born.
- Affectionate Nickname: Willie calls Eugene "Lightning".
- At the Crossroads: The destination is the fateful crossroads where Willie Brown made his deal. Implied to be the same crossroads that Robert Johnson made his deal at.
- Battle of the Bands: The movie is decided in a guitar duel between Eugene and Jack Butler, who is standing in for The Devil.
- Bring It: Eugene does it wordlessly.Scratch's Assistant: (mocking) Well, well, well... who sent you here? Can't talk little man? (Evil Laugh) Bet ya can't play none, either!
(Eugene says nothing, and plugs in his guitar.)
Scratch's Assistant: ... Uh huh.
- Cynical Mentor: Willie Brown is mean, vicious, and biting in teaching Eugene about the Blues. Not to mention he has no problem exploiting Eugene for his ends.
- Deal with the Devil: Willie Brown made a deal with the Devil for his blues. He is now trying to get out of the deal.
- Despair Event Horizon: How Eugene finally plays the blues — losing a woman he was interested in.
- Exact Words: Part of the Deal with the Devil, described above. Willie tries to complain to Satan that he didn't get what he wanted out of the deal. Satan replies that the deal was only that Willie Brown would acquire fame and fortune through his blues skills. He never said Willie would get to keep them.
- I Have Many Names:Willie: What time he coming around?
Scratch's Assistant: (faux confused) What time who coming around?
Willie: You don't be fooling with me. I'm talking about Legba.
Scratch's Assistant: (amused) Legba? Where you been at, slick? He done changed his name to Scratch.
- Kick the Dog: Not only does Legba's assistant convince Willie to sell his soul, but he took the $2 that he initially refused to take to get Willie to sell him his soul!
- "The Reason You Suck" Speech:Willie: You got your mind made up about how everything works. How you gonna learn anything new when you KNOW everything already? (picks up Eugene's old, scratched acoustic guitar) Look at this old guitar here you been squeakin' on. I bet you saw this thing in a music store and bought it just because you thought it was beat up! Well you got it all wrong. Muddy Waters invented electricity.
- Road Trip Plot: The entire movie is Willie and Eugene trying to get from New York City to back country Mississippi to see "the man".
- Rock Me, Asmodeus!: Both Willie Brown and Robert Johnson definitely got their skills from Satan, as did "Jack Butler", the musical antagonist.
- Rock Me, Amadeus!: Eugene defeats Jack by rocking out to electric guitar riffing based on classic music.
- Spiritual Successor: The film has the same basic plot as "The Devil Went Down to Georgia" by The Charlie Daniels Band.
- Technician vs. Performer: This is the conflict between Eugene and Willie. Eugene can play the songs well, and has a fanboy obsession with the Blues. Willie sees Eugene as someone who lacks the struggle and hardship needed to play blues.
- Teeth-Clenched Teamwork: Eugene and Willie. The former is exasperated with the latter's duplicity and rudeness. Willie sees Eugene as a pampered wannabe with no respect for real blues.
- Unusual Euphemism: Willie refers to a penis as a "whip".
- Urban Legend: It was rumored that Robert Johnson, a real life blues guitarist who was self-taught, sold his soul to the Devil, which is how the crossroads legend began. Willie Brown is also based on the same Willie Brown of blues legend.