I wish I could think of one that y'all missed, but the selection criteria make that difficult.
EDIT: moved the biplanes to the lower list
Here is my list, within the criteria:
MiG-3 - I believe it had the worst record of all the Soviet fighters in the first year of the war. Very slow at low altitude and terrible handling.
LaGG-1/3 - Seemed to have the worst production quality of the early Soviet fighters (which is saying something). Too heavy. Eventually improved and also led to La 5 series.
MS. 406 - Good for when it first came out, .
Bloch 150 / 152 - Poor handling, inherent instability, power plant problems.
Fiat G.50 - not a terrible design but too temperamental and fragile.
PZL P.11 - good for when it came out, with some advanced features, but not quite up to par
CAC Wirraway (to the extent it was used as a fighter, though most weren't so it probably doesn't qualify)
Worst if you include biplanes, 2 crew, 2 engines, and / or drop the production criteria to 250+:
I-153 - Used in numbers far too late for a biplane. Too slow. Took horrific losses.
CR 32 - Obsolete by WW2
CR 42 - Obsolete. Came out too late for a biplane. Too slow.
Gladiator - Good design, obsolete by WW2, still held it's own for the first few months
Blakburn Skua / Roc - just barely effective for the first few months of the war, after that it was really marginal. The only thing that saved it was short legs of German land based fighters.
Boulton Paul Defiant - zany idea that was doomed to fail. Turret had some potential but enabling it to shoot forward was too complex. Zany.
Fairey Fulmar - Bad design spec. Not only unable to handle enemy fighters, but too slow and too low flying to intercept enemy bombers half the time. They should have made a few of these for long range recon / navigation / pathfinding, and made a single-seat version with a smaller wing as the main CAP / Escort fighter.
Fairey Firefly - Waste of a powerful engine! Too slow for when it came out!
Me 210 - Bad wing. Fixed (too late) with 410.
P-51A - Poor aileron design contributed to a very lackluster combat record as a fighter. The British had luck with the similar Mustang I (etc.) for recon. Fixed with the P-51B etc.
PZL P.24 - Similar to PZL 11, not quite enough, gull wing design was probably the main issue besides engines
Caudron 710 - Too slow
Me 110 - had potential as a night fighter but it never reached it's intended potential as a longer ranged day fighter and was basically a waste of resources
Ki-45 - similar problems to Me 110
Bristol Blenheim "fighter"
Worst in 50+ category:
VL Myrsky - Bad design all around
CAC Boomerang - bad concept poorly executed.
P-400 - marginal early version of P-39 made worse by design changes and lack of certain parts / supplies (O2)
Obviously some of these were bad because they were just obsolete. They weren't so bad earlier in the war. Others were bad because of just bad design requirements. And others started out bad but got a lot better. There were also a lot of planes which looked like good designs on paper but couldn't be made to function in a war environment. Most of the late war Japanese fighters fall into that category, as do a lot of the German jets and rockets.
I would say the I-16 wasn't quite in the bottom category because though many died flying it, there seemed to be a higher percentage of Soviet pilots (many future aces) who kind of got the knack of fighting with it and managed to score a few victories in spite of it's flaws, and survive until they got something better. The later marks were able to manage over 300 mph, and by the time you get to the later model I-16s with the 20mm guns they were just below the threshold of competitive in the hands of a good pilot. Speed was close and their agility and small size helped (some of) them survive. The I-15 / 153 by comparison was just too slow, hyper-maneuverability helped a bit but not enough to survive that brutal battlefield.
There were also other planes which had a really long and painful teething process, starting out bad though ending up pretty good. The P-38, Corsair, and Typhoon would fit in that category IMO. P-38 issues are well known, the Corsair had a lot of small problems which added up to a maintenance nightmare particularly in the Pacific. Of course it got better though.