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For much of Kim Possible's time at Middleton High School, she was usually the captain of each cheerleading squad that she participated in. She was the captain of the Junior Varsity Cheerleading Squad in her Sophomore year, then she was the captain of the Varsity Cheerleading Squad in her Senior year. It was unclear which squad Kim was on during her Junior year. Bonnie Rockwaller was elected squad captain by popular vote at some point during Kim's Sophomore year, largely due to extensive efforts on her part to both improve the squad and replace Kim. However, Bonnie presumably returned the title to Kim after a very brief period upon realizing how heavy the workload was, as she was never referred to as captain after that point and Kim once again assumed a clear leadership role on the squad--Ron figured that Bonnie would only last about a month while Kim suggested two weeks at the most. It can be noted that Bonnie never again made a point of trying to replace Kim as captain again, although she did continue to angle for prominence during routines.
Ron Stoppable brought the school mascot, the Middleton Mad Dog, to life for his Sophomore and Junior years, which was not only well-received, but gained him some fame among the mascot circles. After joining the football team in his Senior year, he was forced to retire from his mascot duties. At Bonnie's suggestion, Jim and Tim Possible became new mascots, the Pep Puppies, during Kim and Ron's Senior year.
The primary (named) cheerleaders
- Kim Possible
- Bonnie Rockwaller
- Ron Stoppable (former mascot)
- Jim and Tim Possible (mascots)
Additional (unnamed) cheerleaders are:
- Interestingly, the National Federation of State High School Associations (NFHS) uniform regulations basically state that high school cheer squad uniform tops must cover the midriff while arms are at the sides. Thus, it is improbable that any high school in the US would allow the Middleton Cheerleader uniforms in any competitions. Therefore, it is likely that the creators based the uniforms off of collegiate or professional cheer uniforms rather than any high school's uniform.
- This Real Life Ruling for High School Cheerleader Outfits did not go into effect until the summer of 2007. Since the show ran from 2002 to 2007, the MHS Cheer Squad (and the show's creators) were not bound to such limitations.
- Careful scrutiny of the show will reveal nearly 40-some cheerleaders, not counting two seen on the American Dragon: Jake Long Halloween episode.
- Contrary to stereotype of school cheerleaders being mean, rude and snobby, Bonnie was truly the only "mean girl" among the MHS-cheerleaders--pretty much all the others were actually nice, including Kim herself.