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After a misunderstanding about the duo's sexuality, Gary's dad signs him up for the Marines. Gary and Mike are befriended by mysterious stranger when their car breaks down, who tells him he will kill Gary's dad,if Gary kills the stranger's wife. After the wife dies accidentally, Gary must race to save his father's life.
Gary and Mike get a job at Corn Diggity Dog in the Mall of America. A competing company is close to putting Corn Diggity Dog out of business until Gary realizes he has a special skill that can save the business.
While trying to find "The Scene" in Hollywood, the guys encounter an elderly, oversexed actress and a person who might (or might not) be Gwyneth Paltrow.
Mike's ex, Beth (RazorKat's drummer), is getting married. Mike doesn't like the guy, whom seems to have everything. Thanks to some pulp fiction novels, Gary is acting Shaft-like, and helps Mike figure out what Beth's fiance is really about, as Mike attempts to sort out his feelings for her.
After a close call with death, Gary decides he should come clean with his father about his road trip with his buddy Mike. Mike gets them booked as guest on Jerry Springer where the staff lies to the duo about the shows subject mater and ambushes them with Gary's father.
In Minnesota, as Hasselholf's comet nears, Gary and Mike meet up with two girls whom turn out to be part of a cult. Gary wants to get out of there quick, but Mike says he's to close to getting some to leave, so Gary relunctantly agrees to stay the night. Soon, Gary is pulled into the cult with his new name: Ga. Now it is up to Mike, whose cult name is Huh, to save Gary in time.
After arriving in New York City, Gary and Mike's car is stolen. Broke and without wheels, the guys crash a Bar Mitzva where Mike is mistaken for a murderer. Gary blames Mike for their bad luck and leaves. Gary's luck keeps getting worse, while Mike's gets better and better.
It's Viva Las Vegas for Gary and Mike, when Mike sets up a plan to help Gary get rid of his "virginitis" by setting an unknowing Gary up with an escort. Gary thinks the girl really likes him and winds up falling for her, hard. Mike tries his hand at card counting.
Gary and Mike enter the nation's capital, where they're in desperate need of money...so they hunt down a friend of Mike's mom. Soon, they're working on a campaign. Gary seems to be helping a great deal, but without knowing it is causing more trouble than the campaign can stand, meanwhile Mike finds himself falling for a much, much older woman.
Gary and Mike go on MTV's Road Rules and visit Mike's brother, Ben. Ben gets jealous of Mike because he becomes more popular than him, and Gary meets a new "friend".
Gary and Mike find themselves at a Phish concert in Vermont where Gary accidentally swallows a mind-altering drug. When he comes to his senses, he discovers he's married to a 35-year-old hippie woman with three kids. Mike finds out that there is more to festival style concerts than meets the eye.
On their way through the "bible-belt", they stop to get some food. They pull in to a Jesus-themed restaurant, where Gary and a waitress become smitten with each other, but Gary fails notice a mole that covers half her face until its too late. Meanwhile, Mike tries to win a hot rod in a "keep your hand on a car" contest
Gary quits his nursing-home job to follow in Lewis and Clark's footsteps, but his plans change when his clueless pal Mike hitches a ride after fleeing an angry police officer.
