The janky, awkwardly compressed timing of the story. The anachronistic mix of contemporary and modern music. The curious backseating of Penny, who seems like she should have been a much more major character. It all seems like bad writing... until you realize the voiceover from the beginning is a grown-up Frances Houseman recounting her memories, and that the story is how she remembers it, not quite how it actually happened.
During the final dance, Johnny puts on the record of "Time of My Life." During the long instrumental, however, the house band appears to be playing the song, leading some viewers to mistake this for a plot hole. In reality, the band's improvising to the recorded music, something talented jazz-trained musicians could easily do once they've heard the song's basic structure. At Kellerman's, the band's never been required to play anything other than standards, hence Mr. Kellerman's surprise that they seem to already know the song ("You have sheet music for this?"). It's another example of the movie's theme of underestimating people's hidden depths and putting them in boxes: the stodgy house band has a professional jazz background, and in all the time they've worked for Kellerman, he's been completely unaware of it.
Neil says he's planning to join the Freedom Riders the following year, which would be 1964. This is already unnerving considering the violence these activists were subjected to, but recalling the fate of three civil rights workers that summer, is it possible that Neil might know any of the three, or could he even be a Captain Ersatz for one of them?
Or what if Baby might know at least one of the three? Andrew Goodman, one of the victims, was a New York City Jew and the second son of a doctor (as a review of the remake pointed out, he was from a family similar to Baby's; Michael Schwerner was from New York City, too, and he was also Jewish).
The movie is set during the summer of 1963, which some historians have deemed as America's last summer of innocence—by the fall, John F. Kennedy was assassinated and the turbulent 60's kicked off.
the following year, which would be 1964. This is already unnerving considering the violence these activists were subjected to, but recalling the fate of three civil rights workers