Since my Austin Powers suggestions are proving controversial, I will replace them with more age appropriate 90’s-classics - Reservoir Dogs, Se7en, and Pi.
I mean when I was that age I loved Wayne’s World and Terminator 2. Still would recommend the former at that age. Maybe I shouldn’t have seen the latter but it’s still a great film. (The Matrix is probably a safer choice for a kid, yeah, and also outstanding.)
Co-sign The Mask and 10 Things I Hate About You for sure.
I love Billy Madison but it depends on how much your kid likes absurdist humor. Happy Gilmore is probably more of a mainstream choice to give a kid.
I liked a lot of stuff out of my age range though, not sure how much help this is.
Austin Powers is probably fine, Office Space might be a little pitched toward an older audience but there are a lot of good specific, well-caricatured characters that I think anyone could enjoy. Beavis and Butt-Head Do America probably fits that bill too, depending on whether you think the duo are age-appropriate.