» characters · sylvester 'sly' winkle
Sylvester 'Sly' Winkle, portrayed by Michael Cade, is the band's manager, who utters the catch phrase "ba-boom!" (either when he gets an idea, in elation or simply at random) in most episodes, who routinely concocts schemes to make easy money one way or another. Many episodes also involve Sly's numerous attempts to get girls, having attempted to win the affections of Jenny (in season one) and Lorena (in season two) through manipulative means (as examples, in "Dream Man", he tries to remake himself into Jenny's idea of the perfect guy by spying on a conversation with her friends during a sleepover; in "Follow Your Dreams", Sly copies the results of Lorena's career aptitude test to make him a fashion designer, the same career that the test states Lorena is suited for); Sly also dated Tiffani in season one's "Romancing the Tube", while the two become closer after she tries to teach him how to surf. After failing at his earlier attempts to attract Lorena, he falls in love with her after having a series of dreams about her in season four's "Dancing Isn't Everything", only for Lorena to not return his affections then; this changes in season five's "Love Letters", at which point the character begins to be depicted as much less obnoxious and somewhat more charming than previously portrayed as. However, the season five episodes "Mop 'n Pop" and "Father Knows Bets" also aid in this shift in depiction as both episodes acknowledge that he has a strained relationship with his businessman father on account of him being unable to spend time with him because of the demands of his dad's duties as a corporate executive, which stems into Sly's gambling addiction in the latter episode.