Going to give my second vote to who I think has best fulfilled the categories. I'm not a fan of movies being shoehorned into genres they shouldn't really be in. I know Letterboxd is partially to blame for this, but I think it's also on us not to push it too much. Otherwise having categories starts not to matter.
Sorry to Nicholls first of all. He's just unlucky that I never much liked Withnail and I (although I saw it under very strange circumstances, so I should give it another watch one of these days) and I'll be honest I've not seen Blood Simple (will add it to my watchlist). So it's down to Chakan and Dis.
Going 1 vs 1 -
Das Boot > Highlander (Highlander is good fun, but Das Boot is an all timer)
Dirty Rotten Scoundrels > The Hitcher (Love Rutger in everything he does, but DRS is a marginally better film IMO)
Gremlins = The Dark Crystal (Impossible to pick between these. Both iconic 80s adventure/fantasy films. Love them both for different reasons)
Good Morning Vietnam > Scrooged (This is a tricky one, because I love Scrooged but I don't think it's in its best category. I'd say it's more fantasy or comedy. GMV is also an incredible drama film and one of my favourite Robin Williams performances)
This is Spinal Tap > Airplane (This just comes down to personal preference. I 'm a huge music fan and Spinal Tap hits all the right chords for me)
A Nightmare on Elm Street > Little Shop of Horrors (Another toughie, since these are both such different examples in the genre. Nightmare is probably the most iconic horror of the 80s and better at being a horror movie though, so that steals it)
Aliens > The Abyss (Aliens is an all-timer, enough said)
The Princess Bride > Akira (Akira is fantastic, but nothing beats The Princess Bride)
Evil Dead II = Tron (I'm not a fan of gory horror, so it's hard for me to judge this one. I know that Evil Dead is objectively the better film, but I would always rather watch Tron. So I'm calling this a draw)
Chakan wins 4-3! Sorry dis. Could've easily gone either way.