Dan: The main character, a sarcastic, cynical, and overly-competitive man with a huge chip on his shoulder. He has an extreme dislike for anything he perceives as "better" than him, which leads to his constant quest to "win" against the world.
Chris: Dan's best friend, a well-meaning but often oblivious and naive guy. He acts as the voice of reason and serves as Dan's moral compass (though Dan rarely listens). Chris also acts as the straight man to Dan's comedic antics.
Elise: Dan's girlfriend, a strong-willed and independent woman who puts up with Dan's antics. Elise is often the target of Dan's obsessions and schemes, but she also provides a grounding force and shows a surprising ability to see the good in him.
The Narrator: A dry and sarcastic voice-over who provides commentary on the action and Dan's often illogical behavior. The Narrator is never seen, but serves as a running gag and keeps the audience informed.
Other recurring characters:
* The Dan-Bot: A robot version of Dan that appears in several episodes.
* The Dan-Vans: A group of people who share Dan's name (and often his personality).
* The Neighbor: Dan's next-door neighbor, who often falls victim to Dan's schemes.
* The Annoyingly Perfect People: A collection of seemingly perfect people who constantly rub Dan the wrong way.
The show also features various other one-off characters in each episode, often related to the particular challenge Dan faces.