Like the perfect wine and cheese, the strudel with le crème, or the beer with another beer, watching the right two movies back to back can bring out the finer, subtler qualities in both.  That’s why I’ve assembled a list of my personal suggestions for possible double-feature nights.  For the sake of variety (and because I like to challenge myself) I chose to avoid using direct sequels or deliver a double dose of a writer/director in the same pairing.

Get Down!  Get Down Again!  The Running Man (1987) / Total Recall (1990)

I avoided pairing movies with the same writers, directors, or lead actors…with this one exception, because I for a time was not sure which movie was which.  Yeah, Arnold’s action movies are all chock full of one liners, explosions, “babes” of the day, and silly villains with sillier deaths, but these two both throw Schwarzenegger into man on the run situations so similar and satisfying it really is hard to know where one stops and the other begins.
            Which to Watch First?  The Running Man has some of the most groan worthy one-liners you will ever hear, like when Maria Conchita Alonso asks Arnold what happened to Buzzsaw, who was just previously bisected with a chain saw, Arnold replies “he had to split” and his fight with hockey-themed stalker named Sub-Zero is a standout.  Total Recall, for all its 90’s tropes, is still a Paul Verhoven film and has more to it than the simple exterior suggests.  The action matches the fun of Running Man and is guilty of its own terrible lines, but getting those laughs out of the way can help you appreciate the solid qualities in Total Recall.  The ambiguity on reality, alone gives it points for giving its audience some thinking room. The Running Man

Even in the Future Nothing Works!  – The Fifth Element (1997) / Serenity (2005)

These two are an obvious match.  They’re both futuristic, space-based, sci-fi action movies with large, ineffective governments clashing with the little guy and except for only one having aliens, both Besson’s and Whedon’s future visions are very culturally diverse.  The stories differ but the archetypes are familiar.  I could see Korben and Mal getting a drink while Shepherd Book and Father Cornelius discussed scripture, and River and Leeloo finger-painted or beat up tough guys or did whatever two crazy super powered girls would do.
Which to Watch First? I recommend beginning The Fifth Element, and after all the colorful fun, ‘splosions and 90’s end credits music you can jump straight into Serenity’s dustier adventure through the not so shiny future.  Elements of Serenity hit a bit harder as well, so best to save those for last.  The Fifth Element

Huzzah for 80’s Fantasy! – The Dark Crystal (1982) / Legend (1985)

It is hard to think of many quality live actions fantasy films from the pre-CG era, but these two always to come to mind first.  Unlike more memorable fantasy movies in recent history, both of these movies were original stores and not adaptations from source material.  The Dark Crystal highlights Brian Froud’s notable creativity and we are lucky that Jim Henson was there to bring these creations to the screen, and amazingly do so practically.  Legend uses a classic stable of fantasy creatures such as goblins, unicorns, witches, and Tim Curry but through the use of academy award worthy makeup and prosthetic effects that make them more than stock creatures.

Which to Watch First? Ironically Legend is the decidedly darker of the two movies, and I feel the opening music and narration of The Dark Crystal is a good gateway.  Finishing with Legend’s theatrical ending and original closing song by “Tangerine Dream” is more satisfying that Crystal’s successful but strangely somber ending.  The Dark Crystal

You’re not Claustrophobic, Are You? – Alien (1979) / The Descent (2005)

After watching these two back to back, you’ll probably want to roll around in a sunny field full of daisies, because anything darker or more confined will give you waking nightmares.  While the subsequent films in the Alien franchise are all action heavy, our first introduction to Ripley and the Xenomorph is a tense, ominous, horror movie: seven crew members and a killer alien trapped on cavernous space ship where “no one can hear you scream.”  The Descent is one of the best horror films released in the thousands and traps our leads in a literal cave full of hungry mutated humanoids.  The jump scares are typical but predominantly very effective making this a fun one to watch with an audience, but the mental instability of lead Sarah and claustrophobic scenes of spelunking are the most riveting.
Which to Watch First? Starting with Alien will give you an intentionally slow crawl into this pairing, and more enjoyable character time before shit hits the fan.  The melancholic ending will transition well to the jolting start of The Descent and again I will recommend the original UK ending, as it is unquestionably better and may even make you rethink the ending of Alien.  Alien

Video Games and Real Life Had Twins! –  Scott Pilgrim vs. The World (2010) / Wreck-it Ralph (2012)
These two love letters to video games and arcade nostalgia pair well because they are two answers to the same question.  Scott Pilgrim starts off with an 8-bit Universal title and introduces video game elements into the real world of Toronto, and Ralph puts us a world of video games that functions just like real life (sort of).  You’ll have to decide if you’d rather have life like a video game or a video game like life, but if The Sims start playing me I’m going to be worried.
Which to Watch First?  Another case in which I will leave it to your taste.  I would watch the family film first, and then the one made for grown-ups but they’re similar in tone, pace, and length to not make much difference.  Though SP has better music.   What you should actually watch first is “Raiders of the Lost Arcade” segment from “Futurama.”

Band On the Road – The Blues Brothers (1980) / O Brother, Where Art Thou? (2000)

Twenty years apart in the making, and over forty in the setting these two films are incredibly different stylistically, but both have a group of musical criminals (or criminally inclined musicians) on the quest for charity and redemption, evading the law and various other colorful enemies they meet along the way.  Neither are traditional musicals, but both are driven by a vast array of diegetic performances evocative of the locales the bands go through.  They have very different senses of humor, which is why you won’t find Animal House paired with Fargo on this list, but these two form a pair of fun musical episodic adventures.
Which to Watch First? Here I’m really going to say it comes down to taste.  Blues Brothers is the more farcical comedy with an upbeat soundtrack and O Brother is a retelling of “The Odyssey” through the music of the Depression-era American South.  I’d prefer starting with Blues Brothers, but that’s just me.  Tie

Creature Features with Likeable Bait – Jaws (1975) / Lake Placid (1999)

I’m not a huge fan of the run of the mill giant thing wants to eat you type creature features, but Jaws is the oft imitated, never duplicated template that set the bar for the whole genre.  One reason Jaws still holds up, while most others do not, is that the human characters and the creature feel like equals and do not overshadow the other.  Of course the shark is the anti-hero of the movie, getting his own POV kills before we even meet our full cast but by the time Brody, Quint, and Hoop-ah! set out to get him we know we’re in for a fight.  It’s like Rocky II.  Lake Placid plays out more like Home Alone 2, if Kevin was played by Bill Pullman, Brendan Gleeson, Oliver Platt, and Bridget Fonda, and the burglars and hotel staff were a giant alligator.  And Betty White is the pigeon lady.  That cast alone elevates a surprisingly clever script of what I think is an underappreciated, solid creature feature.
            Which to Watch First? It’ll be interesting either way, but seeing Jaws begin so many clichés for its genre and then seeing the next generation’s homage garners more appreciation for the tropes than rehashing them because they ought to.  You also don’t want to go backwards from the impressive animatronic and CG alligator to the barely functional Bruce.  Jaws

The Black and White of Neo Noir – Kiss Kiss Bang Bang (2005) / Brick (2006)

Tonally these movies could not be more different, but they have their roots in similar pulp, noir, detective material and are both revolve around a murder mystery.  They are also both products of a sole writer/director on the project, and I find movies like that tend make more of an impression; in this case KKBB and Brick show how differently Shane Black and Rian Johnson can interpret similar source material, while pulling fantastic performances from Robert Downey, Jr. and Joseph Gordon-Levitt.
Which to Watch First? Brick.  No question that while Brick is a heavy, gritty movie, you will rather take a walk through those grimy streets first to wind up at a Hollywood party with gay Val Kilmer than the other way around.  Brick

Pleasing Your Eye Holes – The Fall (2006) / Pan’s Labyrinth/“El Laberinto del Fauno” (2006)
            Guillermo del Toro’s Pan’s Labyrinth is the more well known of these two, and even though they came out the same year and had many similarities, Tarsem Singh’s The Fall remains largely unknown to people who aren’t Lee Pace fangirls. Both of these films use the imaginations of young, traumatized girls as gateways to strikingly visual fantasy worlds.  Putting these two films from foreign auteurs together is like matching The Wizard of Oz with Alice in Wonderland with more whimsy in the setting than the words.
Which to Watch First?  Most people have already seen Pan’s Labyrinth and even though it is subtitled, while The Fall is in English, del Toro’s narrative is easier to follow and the world is more instantly engrossing.  Pan’s Labyrinth / El Laberinto del Fauno

Non-American Love for American Action Movies – Hot Fuzz (2007) / Seven Psychopaths (2012)
            It can be said that if you’ve seen one action movie you’ve seen them all, but that’s because for a lot of movie buffs they literally have.  I wouldn’t call either of these movies parodies but Edgar Wright’s Hot Fuzz and Martin McDonagh’s Seven Psychopaths have a lot of laughs and fun with honest appreciation for all the good and bad action movies so influential to their careers.  Hot Fuzz calls out its targets by name and is an Easter egg hunt of direct references, while Psychopaths is a more meta deconstruction of the genre and the writing process, but still with lots and lots of violence.  To quote Sam Rockwell’s character, “Life-affirming, schmife-affirming. It’s called Seven fucking Psychopaths!” 
            Which to Watch First?  Seven Psychopaths’ opening scene comparing the deaths of movie mobsters with real mobsters, delivered by Michael Pitt and Michael Stuhlbarg of Boardwalk Empire (a show about mobsters), so quickly sets the course for this movie’s take on reality that I was on board from the first few lines.  While not as dark as McDonagh’s previous film, In Bruges, Psychopaths is big on the death, but the critiques it makes on the genre will be appreciated when revisited in the overall funnier Hot Fuzz.  Seven Psychopaths