Top three NA players at each role, based off skill/importance/accomplishment:
I'm doing 6s only. Fk highlander.
Pocket: Reptile, TLR, tyrone -- Adam = God. TLR is the most accomplished/best pocket for the longest amount of time. Ty gets the third spot for obvious reasons-- the dominant TF2 personality for years/multiple time champion.
Roamer: Wonderwall, Jaeger, DaveAC. I could argue for mackey and Seagull as well, but I'll stick with these three. Wonderwall was a top three roamer for years, multiple ESEA lan appearances, blah blah blah. Jaeger revolutionized the roamer role in our meta. Dave over mackey/seagull because of skill level and length of time at the top. Seagull is by far the best roamer ever, but for this silly exercise he's like Mike Trout in my mind.
Scout: carnage, enigma, cyzer, Oplaid, yz50. Carnage because 8) and https://www.youtube.com/watch?v=_koOG-RHFC4. Enigma is the best scout ever. Cyzer for length around the top of invite and long list of accomplishments. Sam Lingle is known throughout esports as a gaming legend-- we might as well name this fictional hall after him. YZ narrowly beats out Ruwin and Clock. Dude was just so much better than everyone in his prime-- 100 hours of dm a week = godmode.
Demo: b4nny, Plat, dummy. I think all three are pretty self explanatory. SolidSnake and Destro next-in.
Medic: Fragile, pure, shade. Probably the hardest class to only pick three-- Harb/CB/Casey would also be good choices, but the top three are pretty inarguable IMO. :3
Community dudes/dudettes: rk, twitch john, eXtine, Lange. For YEARS rk was the only dude that kept up any coverage for TF2. Twitch john for all of the support/exposure. Jeff/eXtv has brought countless eyes to competitive TF2. Lange for the laundry list of accomplishments/things he's coded. Honorable mentions: Nahanni, klanananananananananan, $al