Audrey and Walter are getting married; while Josh is happy, Drake is bummed. Drake learns that Josh is Miss Nancy, the advice columnist for the school newspaper, and uses this to get a date with Tiffany Margolis, angering her boyfriend, who challenges Josh to a fight.

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Drake and Josh receive a broken-down dune buggy from a friend and fix it up, but are forbidden by their parents to drive it. Drake disobeys them and drives it anyway, injuring himself when he crashes it but keeping his injuries a secret to stay out of trouble. Josh finds out when he gets a call from the emergency room and convinces Drake to come clean. When they turn on the car’s radio, the song Lifestyles of the Rich & Famous by Good Charlotte can be heard.

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Megan films sheepish shots of Drake and Josh while Susan, Drake’s current girlfriend, flirts with Josh. When she kisses him, Drake comes in and she makes him think Josh is the one hitting on her. As a prank, Megan films this and puts this, along with a bunch of other embarrassing shots, into Drake’s music video project, which unknowingly helps Drake and Josh by exposing Susan as the two-timer that she is.

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Josh tells Walter that he and Drake will babysit the boss’s son so that Walter can get a promotion, much to Drake’s dismay. The baby disappears and Josh panics while Drake leaves to play in a concert. However, underlying loyalty compels Drake to return and help Josh find the baby before Walter and his boss return

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Josh gets his first crush on Cathy. While trying to impress her, he accidentally blurts out that he plays guitar, but he really can’t. Cathy wants Josh to play his guitar at her birthday party. However, Drake and his band get kicked out of a coffee shop he plays in due to Megan’s snake, Robert. 

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When Audrey, Walter and Megan leave the house for the weekend, Josh’s grandmother comes to babysit. Grammy makes a deal with Drake- if he beats her at a basketball game, he can go with his friends, but not to a concert. He wins, but once there, finds out the tickets his friends made are frauds, and Grammy has to pay a $200 fine. After losing another basketball game against Grammy, Drake is forced to explain about the concert to his parents, but Grammy stops him, seeing as he paid back the $200 and was willing to tell them, instead explaining that she beat Drake at basketball.

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Drake has an addiction to junk food and Josh has an addiction to video games. One stormy and rainy Saturday, Audrey asks Drake and Josh to pick up Megan from her friend’s house, but when Audrey gets home, she sees that Megan is soaked and then grounds Drake and Josh for not picking her up. The two boys then make a bet that whoever caves first on their addiction has to dye their hair pink.

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Josh gets a job at The Premiere for making “Crazy” Steve (Jerry Trainor) quit after complaining about his wobbly drink holder but Helen soon forgets Josh’s job. Drake soon starts working there, too. However, Drake seems to be stealing Josh’s limelight as a good employee, despite being as lazy as usual. Drake was being adored by the boss, Helen, and that leads her promoting Drake to assistant manager.

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Drake wins tickets to his favorite band’s concert, Zero Gravity, and he also gets an autographed Cherry Red Fender Stratocaster signed by the lead guitarist, Devin Malone. Josh plugs it into Drake’s bad amplifier to show Megan how an electric guitar works, and the guitar explodes. Josh tries to buy a new one and get it autographed before Drake finds out. Meanwhile, Walter struggles to bond with Drake.

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Drake says Josh is uncool after Josh humiliates a cheerleader (Leah Pipes) and makes him try out for the school football team to become popular. Josh becomes the equipment manager, but will have to play in the state finals after his brownies, poisoned by Megan, makes all of the players sick.

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