I'm sure they'd have 2 kids or so and Robbie would be a big time music star.
I would like to think that Billy found Robbie good work as a studio musician/backing vocalist/writer in a comfortable job between wedding gigs. This would be a comedic set up for his big shot as a lead singer.
I could actually see this in two ways. The first would be a sudden rise like Tommy DeCarlo or Arnel Pineda. The second would have Robbie become a surprise competition show contestant. The possibility of combining the two might even be reasonable. Losing the competition, only to be asked to join a top notch band.
Culturally, the competition show angle would be a better fit for a movie though. The Wedding Singer was poking fun of pop culture of the era, so it only makes sense to continue in that direction. If I were writing it, this would be where I would start as a first draft, but I do prefer the idea of a wedding guest "discovering" Robbie as a potential front man for his classic rock band.
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