I know most of this has been covered before in other threads, but that was before I registered, so here's my 2 cents (or 5, we don't have anything smaller in NZ). To make it a little more interesting (or self indulgent) I came up with a few extra categories.
Thus for your consideration I present;
Overall best looking for combining speed, grace and proportion is Concorde. Runner up after a tough decision is the SR-71 Blackbird (Hmmm, light vs dark).
Stealing HCE's categories:
1903-1919 Fokker DVII, Fokker DrI
1920-1930 Bristol Bulldog, Ford Tri-motor
1930-1940 Beech Staggerwing (possibly best looking biplane ever), and yes, Supermarine Spitfire (agreed, Mk IX is probably best looking, but Mk XIV is personal favourite for some reason).
1940-1950 FW190 D-9, F-86 Sabre (first flight '48-49 IIRC)
1950-1960 F-104 Starfighter, Buccaneer S.2, E.E Lightning F.3 or later (definitely heading for best looking rather than beautiful I think!), A-5 Vigilante, B-58 Hustler, F-8 Crusader
1960-1970 Saab Viggen, TSR.2 definitely, Yak-28 series, TU-22 Blinder, XB-70 Valkyrie
1970-1980 F-14 Tomcat, Su-27 Flanker, F-117A Nighthawk (prototype first flew '77 IIRC)
1980-1990 Saab Gripen
1990-2003 F-18 Super Hornet, Su-37 Berkut
Meanest (as in, "you look at me again and I'll come over there and kick your a@@e") looking - Mi-24 Hind 'D' or later, late '70's+ B-52H Stratofortress
Looks too pretty to be mean- F-16 Fighting Falcon, Folland Gnat/HAL Ajeet, Canberra B12.
Looking at it makes you wonder quite what the designers were thinking- P-82 Twin Mustang.
Best 'Thrust will solve all your problems' look- Mig-25 Foxbat, X-15
Most innocuous-but-not-to-be-underestimated looking- RNZAF A-4 Kahu Skyhawk (minus hump).
Most funky looking- Late Su-22 Fitter (swing wings apparently bolted on as after-thought), F 105 Thunderchief.
Most evil looking- B-1B Lancer, Anti-Flash white Avro Vulcan B.2 w/Blue Steel, shark-mouthed USAF PACAF F-4E with wall to wall AAMs.
Looked cool but wasn't really that useful from what I've heard- F-89 Scorpion, DH Venom, Tornado F.2
Least graceful looking- A10 Thunderbolt II, A-6 Intruder, Fairey Barracuda, AW Whitley.
'It just looks wrong'-Supermarine Swift, Yak 38 Forger, FMA Pucara, Mitsubishi F1, SR.53, Gloster Javelin, Boulton-Paul Defiant, any of those wierd hinged wing things NASA used to fool around with.
Doubtless more categories and contenders will come to mind about 30s after I click 'submit' (and I know, there's not a lot of civilian kit there), but right now I'm off to find a shovel and a helmet in case some of my picks are seen as a little inflammatory.
