Tommy, Merton, and their new companion, Lori, find themselves battling against the ghost of a football player who is behind the football team's 61-year-old curse.
When Tommy and Merton enter a wormhole that lets them travel back in time to 1989, a Russian man named Boris follows them and changes the outcome of the Cold War, which leads to the collapse of the United States and worldwide enforcement of communism. Meanwhile, Tommy must decide whether or not to warn his past self about the werewolf attack that will change his life.
At the same time that Lori discovers Tommy's true identity, a group of werewolves called the Evil Werewolf Syndicate decides to force Tommy to join them.
A traveling pro-wrestler named Dr. Apocalypse comes to town. He has racked up 665 wins--but the six hundred and sixty-sixth could cause the end of the world. To save the universe, Tommy, Merton, and Lori have to prevent Dr. Apocalypse's next victory.
Tommy and Merton are put up against the villainous Sandman, who enslaves sleeping people in an attempt to get them to touch a special sand that will put them to sleep forever.
Tommy and Merton defeat who they believe is a demon trying to attack an innocent teenager, only to learn that the supposed demon is a demon hunter and the supposed innocent teenager is a demon.
While donating items to a toy drive, Merton and Tommy unwittingly release Merton's old imaginary friend, Vince, from Merton's old toy chest. Merton doesn't want an imaginary friend anymore, causing Vince to set out to destroy the Pleasantville Trio.
Tommy finds a stray puppy and is then found by Tim and Travis, who are still hunting for the Pleasantville Werewolf. While dealing with that, Tommy fails to realize that his new puppy is Cerebrus, the three-headed hound of Hades.
Merton creates an intelligence potion after a MENTA, a society for geniuses, rejects him but Tim and Travis soon get their hands on the potion and become smart enough to figure out who the Pleasantville Werewolf is.
When Tommy stops hanging out with Merton in an attempt to win the title of Homecoming King, a group of black-clad teenagers take a liking to the lonely Goth, and offer him a place in their gang. But when they give Merton a nectar that makes him balloon to an obese size, Lori and Tommy realize that the teens' interest in Merton is more like a hunger.
To impress a girl at school, Merton gets a job as a test-subject at a laboratory, which has some literally ugly consequences when Merton is turned into a caveman through sensory deprivation and strange chemical injections.
Death returns to capture Tommy, but in a last attempt to save him, Tommy, Merton and Lori go over all the good things the group has done over the past two seasons through the use of conveniently culled clips.
