FloJack's is packed - only because, in his determination to win a record deal, Craig has sent out letters to all the A&R guys in Chicago and drink coupons to all of FloJack's regulars on school stationary - free postage. But only one A&R guy has shown up: boozy, crusty British rock star Neville Rex, who apparently loves Nasty Delicious. When he finds out Craig is a school teacher looking for a record contract, Neville proposes they help each other out, since he needs to perform some community service to expunge a police incident.
Craig asks Principal Taylor for permission to have a world-famous rock star visit his class, just as Ben shows up with a besotted Neville, who instantly recognizes Eileen "Tight Fit" Taylor as his former groupie/girlfriend. Craig apologizes - he didn't know about Principal Taylor's scandalous past - but she's weary from staying up all night to work on the budget and orders Neville off the premises. Nevertheless, Craig presents his underwhelmed class with Neville, who starts off with a community-service type message, "Don't do drugs..." unless they're uncut and come from a known source! Just then, Principal Taylor pops her head in, and Neville proceeds to tell the class that when they were in love, she inspired him to write his mega-hit song, "Kiss Me, Spank Me, Love Me." Principal Taylor only remembers the not-so good times, like doing lines off the toilet seat at CBGB, a memory that elicits groans from the class. On the way out, Neville asks Craig to set him up on a date with Principal Taylor; his record deal depends on it.
Craig asks Principal Taylor to give Neville another chance, but she has the biggest budget meeting of the year in the morning, and dates with Neville tend to unravel into the wee hours. Maybe Neville could make a donation to the school and help solve the budget crisis? Besides, Principal Taylor isn't a groupie anymore... Catching the spirit, Principal Taylor agrees to have dinner with Neville for the sole purpose of taking his money. But the next morning, Principal Taylor is nowhere to be seen... until an awesome guitar lick blares out of the PA system. Supervisor Dalton, Craig and Victoria find the principal dancing on her desk to the strains of Neville's new song, "I Had Sex with Your Principal." When she thanks Craig for putting her back in Neville's life, Craig is sure he's going to hell, and Victoria just shakes her head.
That night, Craig invites Neville and Principal Taylor to FloJack's, where he surprises them with a new song about going separate ways, featuring Supervisor Dalton on bass. Record deal or not, Neville should want what's best for Principal Taylor, and everyone agrees she needs to keep her principal job. Neville confesses that he needs Eileen. She's his muse; he hasn't had a hit since she left - and finding her was the only reason he hooked up with Craig in the first place. When Craig tells Neville to shove his record deal, Tight Fit becomes Principal Taylor once more. There's no way she's gonna let anyone hurt one of her teachers!
