What are the BEST appearances of Bowser in the Mario Franchise?

Andy 28!

Goomba
I think is Super Mario Galaxy, he really took seriously his plan without joking and you can see how powerful is when he is decided to defeat Mario, the cinematic of the UFO is absolute cinema, probably the best Bowser battle in the main games, and he isn't fine only with defeat Mario and kidnap Peach, he's DESTROYING THE UNIVERSE so the battle feels like if Bowser wins is the end of the world, also in Bowser's Fury he has one of the best appearances and he only wants destroy Mario and nothing more cares about even his Son, but I don't think that is his best appearance but if you think that I totally understand why. Also in Bowser's Inside Story has a really good retreating of Bowser and the same goes for Brothership.
 
The best portrayal of Bowser in my opinion HAS to be in the RPGs. While most games has him be the titular villain, here he can be the butt of the joke at times. Bowser's Inside Story and TTYD has this the best, as they both involve him getting involved in all sorts of goofy shenanigans throughout the story. I know I didn't play Brothership past Bulbfish Island, but while hard to follow along, I like him here too. And considering how much I trash Origami King, I like him here also. Like King Olly, I have my gripes on his screentime.
 
The best portrayal of Bowser in my opinion HAS to be in the RPGs. While most games has him be the titular villain, here he can be the butt of the joke at times. Bowser's Inside Story and TTYD has this the best, as they both involve him getting involved in all sorts of goofy shenanigans throughout the story. I know I didn't play Brothership past Bulbfish Island, but while hard to follow along, I like him here too. And considering how much I trash Origami King, I like him here also. Like King Olly, I have my gripes on his screentime.
I don't have TTYD and I know some things but I don't want to see spoilers because I'm trying to get the remake, his appearance in Origami King is really good he made me laugh a lot specially with the phrase "What a weird family" to Olivia and Olly, and in Bowser's Inside Story I need to explain? He's the MAIN CHARACTER (with Mario and Luigi).
 
It's Mario Party, especially his Mario Party 4 appearance. I firmly think it's one of the most terrifying in the series, whenever you land on his space, there's a lot of tension because you don't know if it'll be just a Koopa Kid or him himself (sometimes Koopa Kid spawns and then Bowser smashes you anyway). And the Bowser minigames he forces you to play *has* to have a loser, so it makes these minigames incredibly terrifying even if the penalty isn't something much, because you don't want to be THAT loser.

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his appearance in Origami King is really good he made me laugh a lot specially with the phrase "What a weird family"

I'll second this. The recent RPGs - particularly Origami King and Brothership - have done a great job with Bowser. They've struck a good balance between making him feel menacing and like a serious, powerful threat (to the Bros. and to other villains!) while keeping his goofier side intact. On top of it, they've added a sentimental side to him that comes through in his care for Bowser Jr. and for his minions.

I had a lot of quibbles with Brothership, but I found its handling of Bowser unassailable. It's exactly what I want out of Bowser when he's not being the final boss or joining the heroes.
 
I really liked how in Brothership was fighting against Zokket and didn't care about how Reclusa was the real villain, and how he can be when is allied with Mario like Bowser's Inside Story and Super Mario RPG, he never is like is a Mario friend he is just like "I'm the villain and nobody else can be better than me" he's fighting for his castle in Sparks of Hope and RPG, Bowser saying "I don't want" when he's being welcomed to save the world with Mario and Peach is so funny. Apart from the RPGs he's a really good villain for the Mario Party series, this feels more appropriate to Bowser than he's appearances in the Mario Kart series, he feels powerful and the minigame "Bowser crashers" of Jamboree is awesome!
 
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i definitely think the rpgs where he's not the main villain is where he shines the most. don't get me wrong he's great in pm64 too but i think he just becomes so much more interesting when not constrained to the expectation that he has to be the biggest threat in the game. from having him as a party member, to one of the main protagonists straight up, to being a recurring NPC who's not allied with any other factions. as long as he isn't the sole antagonistic force in the game he's great (out of games where he is the sole/primary antagonistic force, PM64 is the only one that lands well, the rest all actively make sure the entire cast is just the same as in the mainline games and that's so boring)

The wild card where i'm completely torn on is Dream Team. Bowser being a twist villain is genuinely an interesting mixup, but it came at basically the worst time where the future of original antagonists was uncertain after Sticker Star (you really had to be there). My expectations were high for Antasma to stick the landing, and i felt like Bowser hijacking the plot caused him to not get that chance. Plus you know, BIS had me full in on Anti-Hero Bowser mode. I'll take a thousand Dream Teams over Paper Jam though.

Generally speaking Bowser as a main antagonist has gotten tired to me, he's the antagonist of the status quo which makes him feel more like the straight man compared to other villains, who force him into roles that actually mix things up. I'd absolutely love to see a mainline game where he plays a supporting role and a new villain is the main threat. Heck make it like SM64DS but with Bowser as one of the playable characters, Odyssey has the framework for how he'd play already. Imagine facing off against the final boss as a character that actually can clap back in the pre-fight dialogue.