Drake and Josh make a bet to swear off junk food (Drake) and Video Games (Josh). Megan makes both of them swear to dye their hair pink (whoever loses). When Drake and Josh's mom and dad discover them making a bet, they make a bet as well. When things get crazy, Drake and Josh can't hold onto their bet much longer and decide to break it.

Drake finds out Josh is great at pool or billiards as Josh calls it. Drake bets some kids, and takes advantage of Josh's pool skills and starts hustling people, by taking their money, shoes and other clothing/personal items. Now Josh has made the ultimate bet, and Drake's stuffed in the corner pocket.

Drake has a girlfriend named Kelly who has a laughing problem. He really wants to break up with her, but can't. The reason why is because she is the daughter of Drake's mean teacher, Mrs. Hayfer, who threatens him with summer school if he breaks up with her daughter. Meanwhile, Josh gets a very ugly shirt which he claims as good luck.

Drake is getting tired of hanging around with Josh all the time. So Josh finds a friend named Drew who looks just like Drake. Drake feels he is being left out because of Drew, so he finds his own friend named Jerry who looks and acts like Josh.

Drake and Josh enter a salsa contest so they can win a 45 inch high depth Yatzubishi plasma screen TV. But they won't let Megan join their team, so she decides to play dirty. After she gets the boys in trouble twice and she makes her own salsa, she buys the ultimate target for Drake and Josh. The Peruvian Puff Pepper.

Josh's e-pal, Yooka, is coming from Yudonia to visit Josh. Drake doesn't care about her at first, but then he sees how hot she is. Josh overhears Yooka telling her parents she is homesick, so he arranges what he thinks is a friendship ceremony but is really a marriage ceremony.

When Josh recieves a foot injury, his parents take him to the hospital. While at the hospital, Drake poses as a doctor to impress a bunch of nurses. Then another doctor comes in and thinks he is a famous doctor. Because of this, he has to perform a foot surgery. How can Drake escape without being revealed of breaking the law?

Mindy invites Josh over to her house for dinner and to meet her parents, but things don't go well. Josh hosts another dinner at his house to try and impress Mindy's parents to make up for last time. He asks Drake to not mess up his date. Meanwhile Drake and his new girlfriend, Lucy, wrestle to see who is tougher, to prove that some girls are tougher than boys.

Megan buys a pregnant sheep and makes Drake and Josh take care of it, if Megan Promises to not pull any pranks on Drake and Josh for awhile. But when they see what a pregnant sheep can do, they don't want it much anymore.

To keep from being sent to remedial English, Drake agrees to mentor a little kid named Sammy. Unfortunately, Sammy would rather hang out with Josh.

A new roller coaster is coming out called, the Demonator. Drake and Josh want to be there the first day it opens. But when they get in line, their wild adventure starts.

Drake and Josh go on the Dr. Phyliss Show and relive some of their most outlandish moments. Some will jab at your funny bone, while others will tug on your heart strings.

Drake and Josh are on their way to a family wedding in their car. Unexpectedly and in the middle of nowhere, the car breaks down. This wouldn't be much of a problem, if it weren't for the fact that they're the ones bringing the cake to the reception.

Drake and Josh enter a "Pump My Room" contest to try and redecorate the living room as an anniversary gift for their parents. When they come back to the house they realize that everything is gone. To get the furniture and everything else back, Drake and Josh get a job at a sushi factory, but come home to see that everything is back.

The whole gang has gathered at Drake and Josh's house before Drake's big concert, but thanks to Walter's poor weather predictions they end up stuck in the house due to severe rain. Sure, it's raining outside, but the real storm for Drake to weather is when his new girlfriend meets his exes.

Drake and Josh accidentally kill Megan's hamster and they think she is planning revenge.

After the boys get in trouble for using Fake ID's Audrey and Walter fear they will fall to a life of crime and sign them up for a “Steered Straight” program, but things start skidding out-of-control when a real criminal befriends them.

It's the end of an era. After Josh ruins Drake's chances at having a hit song in the Superbowl, the boys must find a way to make things right.

Josh decides to enter a local dance contest, but when Drake realizes he's going to fail gym, he has to enter in order to receive high school credit. So he steals Josh's dance partner, and that's when things start to go wrong.