One of the more basic principles of comedy is that the right reference will turn an okay joke into a killer. For example, once I was at a party where a drunk guy with a douchey goatee walked up to my friend Billy and asked him, "Where'd you get that tattoo? It looks like a prison tat." Now there are a lot of ways that Billy could have responded. He could have just said "fuck off!" - which would have gotten the job done, but wouldn't have been funny. My default answer would have been to say "Nice chin scruff, Ethan Hawke" - which would have been sort of cutting, but Ethan Hakwe is low hanging fruit for a facial hair based put down. Billy's answer was better than either of those. He responded "Where'd you get that facial hair, at a Muskateers convention?" It was an amazing comeback, because it was appropriately derisive and it was such a smarter reference than "prison tat".
Unfortunately, the flip side of that comedy principle is that the wrong reference will take an okay joke and ruin it. For example take Wayne's World 2. This is a comedy from the early 90s, and if I had to pinpoint one reason why it's continually fails to be funny, it would have to be because the film's references were dated when it originally came out, and now that it's aged for an extra twenty years many of it's jokes are so outdated that they barely make sense.
For instance: the film opens up with two guys named Wayne and Garth who host a local public access show about music going to an Aerosmith concert. Aerosmith? Really? Their presence in this movie feels less like a writer saying "you know who is inherently funny? Aerosmith!" and more like a marketing guy saying "you know who would promote cross brand synergy? Aerosmith!" (Their presence feels even more like a marketing stunt when a second Aerosmith show closes the movie.) The band adds nothing comedically to the scene they are in, but they do make Wayne and Garth seem really out of date, because Aerosmith wasn't cool in 1993; all of the cultural momentum at that time would have been behind grunge, which basically doesn't exist as far as the movie is concerned. An Alice in Chains reference would have gotten dated, too, but it would have at least made sense, because that's the sort of band that's still associated with this era of music.
The reason why the film closes with a second Aerosmith performance is because the movie's main plot concerns Wayne's attempt to put on Waynestock, a big concert in his hometown in Illinois, and Aerosmith is the only band that ultimately agrees to play. Now, leaving aside the question of whether or not trying to put on a concert is a compelling plot (...which it isn't; there have been way too many comedies where the whole point was to put on a big show so they could save the orphanage or whatever...) building your plot around an event that name-checks Woodstock is another "really?" moment. Woodstock has been mythologized so much that it feels like a cliche now, and basing Wayne's aspirations on such an overworked bit of nostalgia helps make the movie feel cheesy. Even worse: it also makes him seem really old, because Woodstock is a touchstone for the Boomers, so it's a generation removed from where Wayne should be.
I keep touching on the character's ages. There's a reason: a large part of the movie's tone deafness is probably due to the fact that in the original Saturday Night Live skits that created the Wayne and Garth characters portrayed them as awkward teenagers, and I don't think either character aged at all when they made the jump to the big screen. That's just nuts; the two lead actors are obviously waaayyy too old to be talking about how proud they are to have finally moved out of their parent's basement, or to be discovering what sex is like. I could kind of forgive the movie's off-kilter pop culture references if I just imagined that the movie was ten years older than it really is, but there's no way I could ever pretend that these thirty year old men were really the age they are acting.
The other issue that has to be addressed is how broad Wayne's World 2 is. This movie features several extended parodies of some classic movies, and every target is Aerosmith-level obvious. When they went into a church I knew a joke about the Graduate was not far behind, and the instant I saw a cup of water on a car's dashboard I knew a Jurassic Park gag was coming. Neither parody subverts it's subject matter at all - they just re-enact those scenes with more mugging, which would be tedious even if those weren't painfully easy set ups. There's also a running gag about how Wayne is shepherded along his journey by a Native American spiritual guide, a la Jim Morrison in Oliver Stone's The Doors. That joke manages the incredible feat of being both too broad and too deep - at the time this movie that movie would have been so fresh in people's minds that a reference to it would have been eye roll inducingly easy, but now that The Doors has more or less faded into obscurity, it just feels inexplicable.
Overall, this movie just feels tired. The writing is easily the worst offender, since the script doesn't want to go one step farther than it has to and it settles for lazy references even when better ones are readily available. But the characters themselves also feel tired, since the specific niche they were built to occupy was already a little past it's prime even in 1993. The sort of dunderheaded rock guy that Wayne is personifying was an increasingly rare breed as grunge picked up steam, and it's almost completely nonexistent now that rock music is barely a cultural force. Wayne's World Two proves that if you're going to riff on something, then don't use something from the very recent past; you aren't going to have enough distance from it to be able to distill it down to it's most perfect components. It's much better to reach back a little farther and maybe a little deeper to pick something you can recontextualize in a fresh light. Like, say, old spy movies from the 60s - or the 3 Muskateers. If there's one thing that I've learned it's that you can never go wrong with a 3 Muskateers joke.
Winner: The Cat