Like a kiddie ride at the county fair: somewhat fun, but comes up short of a "thrill"

Rating: 6/10 (13 June 2019)

This movie is a rather obvious product of a washed-up 30-something nostalgic for the glory days of late high school/early college. Given the pace and pop culture of everyday life in 1998's America wasn't yet all that different from what it had been in 1985 (though consumer purchases were more frequent and bigger-ticket and the music scene a bit drowsier thirteen years on), there wasn't much room to do anything imaginative with the film's setting, which allows for at most some funky hairdos and a few references to the specific pop entertainment acts of the time, not all of which hit the mark.
(On the other hand, Alexis Arquette as an obsessed perennial Boy George LARPer was perhaps an appropriate touch - well, about as "appropriate" as one can get in a movie destined for cinemas planted in single-family-unit-dominated neighborhoods - for paying tribute to an era. My, how the times have changed! Nowadays any movie which portrayed androgynous behavior as anything but supremely normal would never make the censors today. The Catholic Legion of Decency in Golden-era Hollywood clearly had different priorities from those of the thought police of our day, but I don't think they were ever anywhere near as hammer-fisted.)
So the treatment needed to be put on hold for another 15 years, at least, but it also needed a more imaginative writer. The plot is a completely formulaic and predictable mishmash of love triangles and early-adulthood angst. Unable to really milk its still-green period's idiosyncracies, the film appeals for humor to the lowest common denominator of the time of release (although, this would quickly be relegated to the ranks of the much tamer after the following year unleashed upon the world the likes of 'American Pie' and 'Austin Powers: the Spy Who Shagged Me').
However, all is not in vain. The main characters are for the most part fun and charming. Drew Barrymore and Christine Taylor ooze charm and sweetness as the cheery waitress heroine and her free-wheeling cousin, while Adam Sandler proves he can convincingly portray a "normal" boy-next-door lead. Matthew Glave as the self-inflated fiancé isn't given much but has fun making his character as loathsome as possible; the female variant by Angela Featherstone is equally delightful to hate, probably the brightest spot in the movie, to be honest. Too bad you can count her minutes on screen on your hands.
Overall, worth your time if you want some light fare and really cannot think of anything else to watch. The musical nostalgia aspect has aged well enough, even though with hindsight the soundtrack didn't necessarily incorporate the songs or artists with the most enduring legacies (and some of the best ones they DID include didn't make either of the accompanying soundtracks). Still, I wouldn't mind seeing a more thoughtful 80s-set romantic comedy with a bit spicier period music, sharper idiosyncratic references and a bit of commentary on the period contrasts (mostly in favor of that period against ours, but those who know my sociopolitical leanings won't be surprised I tend to think the past was better). I think such a piece would be pretty marketable. Hollywood, you listening?