He first appears in his living room when he sees his dog wearing dark sunglasses while watching a music video. He attempts to grab the remote to change the channel but his dog grabbed it. During which he came up with a plan; he grabbed his sax and played really loud, resulting in his dog taking his paw off the remote, and taking control of it. As he change the channel, he sees Minnie Mouse in a commercial where she shows clips of Max as an example of someone who is embarrassing, act as a nerd and having life pasting them by. Having seen the commercial Max is given the phone by his dog and decide to call the number and head towards Minnie Mouse Center for the Totally Unhip.
Later he arrives at the Center where upon entering he encountered a women who, at first rap a song to him and discovered that he has no rythem, wears a pocket protector and need a full crash course, She then introduce herself as the director and take him to begin to be hip.
During the way he sees Donald as a wardrobe manager, then meet Vanna White and Pluto as they are in a indoor drive-thru room where she told Pluto to watch the movie and he licked her.
Maxwell is then pulled away as The Director, and Told that he if follows Minnie's intructions, his dull life will be upside down. Then he sees Goofy as a fitness instructor, in which he is place in a room with a lot of TV sets and was left alone until he saw the owner of the Center: Minnie Mouse who kept asking him if he want to be hip, which frighten Maxwell at first as he said he doesn't want to be Hip anymore, until the real Minnie Mouse showed up and kicked the screen, which surprise Maxwell as he is shown a flashback video of when Minnie wasn't hip but a nobody. Having seen the video and about to cry, The Director arrived and after seeing Maxwell falling on the ground, she showed him clips of her friends as clumsy as him, which he laughed.
The next lesson for Maxwell is teaching to dance so he wouldn't be clumsy, to the music "Neutron Dance", In which afterwards as he is about to kiss the Director, Minnie appeared and told Maxwell how nasty boys are not hip, while sawing clips of Peg-Leg Pete to the song "Nasty Boys" which Maxwell laughs at first but then stopped when clips of other Disney Characters at their worst is shown.
After being asked how he felt after seeing the video, Maxwell couldn't come up with the right words to explain how he felt then asked to sing but it turns out he can't seeing right, So Minnie and The Director told Maxwell he needs confidence, in which after seeing a brief clip of Minnie and Mickey singing, He was shown a music video of Minnie and Sir Elton John, in which he was told his next lesson is Romance, As the director change from her geeky self to a attractive look and took him to the drive-in room and Maxwell kept talking about this being his first date and he behavior, but the director stopped him and gave him instructions of how to act on a date, while at the same time he kept ruining the course, which he stopped when they watched more disney clips about dating, he then asked if he could go out with her again but she informs him the policy of the Center is that Employees are not allowed to date clients.As Maxwell plans to give up on romance, The Director told him to keep watching as the best is yet to come. After seeing clips of couples getting back with the song "Jealousy & Making Up" (played in the beginning of the special) After finishing the video Maxwell called the director beautiful and said she look Suzanne Somers (who she really is)
Later Maxwell came out wearing the same clothing as Eltron John while singing "Don't Go Breaking My Heart" which the Director order the female employees to give Maxwell the ultimate makeover, to the song 'Shopping', In which after coming out looking like a new him, Maxwell realize he's done with the lessons and ready to go out in with his new self but admit he's afraid to go because even though he looks hip, he's still the same nerd but After seeing a video of Donald and Walt Disney, Maxwell now learns to be himself (after making a joke about talking like Donald) afterwords he got his diploma and graduate as The Director, the female employees, and Maxwell dance to the song 'I'm so Excited' while more Disney clips are being played as he leaves the center to being his new life as a cool hip guy.
- This would be Robert Carradine first disney appearance until 2001 when he plays would play both Don Keeble from Max Keeble's Big Move and Sam McGuire from Lizzie McGuire
- Many people believe that Maxwell Dweeb is base on Robert Carradine's character Lewis Skolnick from Revenges of the Nerd film series due to their similar appearance, and laughter.