Full disclosure: I am not a Sandra Bullock fan. Whilst I think she can definitely act well, there's something about the way she chooses to portray characters that just takes me out of a film and irritates me. As a result, I'm a little biased.
That said, I did enjoy Miss Congeniality... just about. At the core is a fun premise with a decent execution, but I wouldn't say the film has aged that well. The script, plot and, particularly, the humour feels very '90s and not in a good way. As a whole, the film seems to simultaneously embody the zany, whacky vibe that the 90's committed to in a big way whilst also attempting a more self-aware type of humour, which became popular in the early 2000s. Given the Millenium release, that makes a lot of sense, but the result is a film which is too whacky to make the self-awareness stick, whilst constantly calling to attention how ridiculous it is.
There's also the other spectre of the '90s looming marge: Girl Power! The film goes out of its way to be Modern and Feminist and embrace the same values as ladette culture, meaning a brash mouth and openly gross female lead. Bullock isn't just pretending to be "one of the guys" to fit in or advance her career, she just genuinely is one, being so painfully macho that she's frequently the most "manly" agent in the room. At the time, this hit a societal trend that would have felt refreshing, genuinely modern and actively progressive. By current standards though, it feels a little misguided and blunt. It's still clearly a lot of fun from a female perspective and at no point comes close to true sexism (in either direction), but there are plenty of moments which made me cringe or feel a little uncomfortable. Some of that is hard to pin down, and Miss Congeniality definitely gets points in eschewing a lot of Hollywood gender stereotypes, but I can't feel fully comfortable with what happens. At the end of the day, Bullock's character still has to go through a process where she realises that she isn't truly 'complete' as a woman unless she embraces her feminine side. That would be an acceptable critique on the trope of women having to be uber-manly in order to be treated with respect, but her character isn't set up as someone who is having to play a role at work to get by. Far from it, we see her male colleagues accept her completely, with the only person standing in the way of career progression being herself (also a bit of a stupid plot device) and through the use of flashbacks we know that she has had a typically masculine personality since she was very young. So instead the film tells her that, despite being exactly who she is (a weird stereotype of Girl Power), she needs to become more feminine, interested in hair and makeup and shoes, in order to be fulfilled. Oh, and she needs to find a man. So yeah... there are points here for progressive gender ideas but also some pretty large problems.
Putting that aside, the film holds up well enough. The plot is genuinely ridiculous and the main villains explanation for attempted murder is never more than "woman scorned" syndrome (albeit scorned by an employer rather than a lover), but the characters you meet along the way feel real enough to keep you invested. The story plays out by the numbers, but the script occasionally sparkles, with some genuinely funny moments. The action is a little clunky but never distracts, much like the soundtrack. Plus, overall, the cast is great and provide perfectly enjoyable performances (particularly if you don't cringe every time Sandra Bullock starts hamming things up). Miss Congeniality is a fun film with enough positives to be worth watching, but I can't say there's anything here that makes me want to watch the sequel.