A comedic biopic focused on the life of fictional jazz guitarist Emmett Ray. Ray was an irresponsible, free-spending, arrogant, obnoxious, alcohol-abusing, miserable human being, who was also arguably the best guitarist in the world.

Tom (Joseph Gordon-Levitt), greeting-card writer and hopeless romantic, is caught completely off-guard when his girlfriend, Summer (Zooey Deschanel), suddenly dumps him. He reflects on their 500 days together to try to figure out where their love affair went sour, and in doing so, Tom rediscovers his true passions in life.