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How to get close to a guy I rarely see?

There's this guy I want to get to know who's a grade higher than me. he hangs out with a bunch of the "popular" people (who I absolutely hate, and they hate me, no questions asked). He eats lunch with them, talks with them during break, etc. The only classes I have with him are my study halls - and I do the same AP as him (during those study halls). And in those study halls are the same "popular" people. I used to have an invite to go with a group of people from school (containing those "popular" kids) to a bar or something, but I don't know if I still can.

Ok, now a bit on our interaction. when I do talk to him, it's more like him talking to the whole study hall (yes we have a small amount of kids and no teacher there) and then including everyone in the conversation. He's funny and doesn't mind looking in my eyes when we're laughing about something he said. (but I think he does that to everyone- although I get a nice feeling when we have eye-contact.)

so my question is: any ideas where I can fit more talking-to-him-time? and what I could talk about? and how I can get those clingy "popular" kids off his back?

How to get close to a guy I rarely see?
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