I decided on this film knowing not very much about it other than a few friends of mine being excited about some of the names involved – many of whom are significant figures in the alt-comedy scene, as well as a few higher-profile celebrities like Kevin Smith and Ivy Wolk. I was introduced to a bit of Nick Corirossi’s work as well prior to this, who has done lots of sketches and bits where his “meta-ironic” or “post-ironic” brand of comedy is in full display. He even has a YouTube channel of fake mobile carrier ads as well as a fake political talk show sketch as “Craig Healy” which satirizes the political talk show format.

That style of humor definitely becomes the entire impetus of The Napa Boys. Reading the description of its TIFF webpage might seem confusing at first, but really the main idea of the film is that it’s meant to be a “parody sequel” to Sideways, the Alexander Payne movie that came out over 20 years ago. The two lead protagonists, Miles Jr. and Jack Jr. are dressed and presented in a way that is meant to evoke the characters of Miles (Paul Giamatti) and Jack (Thomas Haden Church) from the original Sideways. There are definitely a number of other references to the original Sideways – the winery setting, the dialogue about wines that feels satirical of the writing, and the general ridiculousness of the plot as a whole involving a wine competition among these different characters and wineries. You get a sense that there’s something silly even about the original Sideways and how so much of that film focuses heavily on wine especially with the character of Miles (even if my overall positive feelings for the original Sideways remain untouched). The Napa Boys also pretends that a film like Sideways has spawned an entire franchise full of Napa Boys comics, plus the opening title basically lists this as Napa Boys 4 (which I guess must be a reference to the first Star Wars movie being Episode 4).

It’s a pretty random film to satirize, and there’s a sense that the film is very tongue-in-cheek about its own satire. It’s shot very much like an SNL skit extended out to a feature, plus there are plenty of gags here that work well on their own – the “shit cum” wine joke that made me (and others) gag, plus one of the waitresses going off on a diatribe about how important being a waitress was to her whole life was also hilarious. I mentioned Ivy Wolk previously and her small appearance and reveal as an incel school shooter was also pretty funny and got a huge response from the audience. Jay and Silent Bob are also there as random cameos which as a side-note makes me wonder if that makes this film part of the View Askewniverse. Simultaneously however, I kind of wondered whether or not there was more to the jokes than just that – hence the post-irony that extends beyond anything Wet Hot American Summer ever did. Was I laughing just because other people (who may be fans of these particular comedians and stars) were laughing? Or did I genuinely find it funny? Was it being a satire of other satires? I cannot tell. There were certainly other moments and references that I didn’t quite get that others in the audience seemed to have gotten.

But I had fun, and this wasn’t quite a dud unlike some other responses to this that I’ve seen, so what more could you ask for really? My favorite Napa Boys movie ever out of all of them. I’m definitely excited for the spinoff sequel The Napa Girls and the upcoming Napa Boys 5 now – hopefully those come out sooner rather than later.