Movies I think pair well together as a double bill or movie night.
  1. Deadpool & John Wick
    Heavy on action & violence, but both fresher and more fun than most.
  2. The Social Network & Steve Jobs
    Both from screenwriter Aaron Sorkin, both films about real people that heavily influenced our world. Different in tone and scope, but still tackle many of the same themes of innovation, pursuit of greatness, and how complicated that is.
  3. Trainwreck & Obvious Child
    Two interesting, funny, smart, and unorthodox rom coms from a very strong female POV.
  4. Honey I Shrunk the Kids & Marvel's Ant-Man
    A contrast in practical vs CGI effects for human being shrinkage. Both are fun and you can swoon over Amy Szalinski (GIFed here) and Paul Rudd (GIFed many other places).
  5. The Wedding Ringer & Wedding Crashers
    R-rated comedies that mine the fertile territory of Weddings, specifically when one or more of the party is not being honest about who they are.
  6. Die Hard and First Blood.
    Both have everyday heroes fighting a system all by themselves. Both slightly unrealistic. But the blood and pain come off as more realistic than most action movies. Plus young Sly Stallone and Bruce Willis to cheer for. Plus sequels if you are so inclined to follow up!
    Suggested by @solitarygigi
  7. Man Hunter & Red Dragon
    Same story based on the Thomas Harris novel "Red Dragon" but made about 15 years apart. Decide if director Michael Mann or Brett Ratner made the better version. Both of course feature the famous character Hannibal (Lecktor) Lecter.
    Suggested by @kiraandlulu