By worst I don’t mean two bad movies. I mean two movies that are so unlike each other that “What the fuck were they thinking when they put these two movies as a double feature??”.
What brought this to mind was a friend mentioning that they once saw “The Producers” on a double bill with “Charly” (the one that came from the classic science fiction story “Flowers For Algernon”.
For me, it was a drive-in double feature of “Halloween” and “Sgt. Pepper’s Lonely Hearts Club Band”. BTW, it was the latter that gave me nightmares, not the former.
My parents did not like drive-in theaters, but one summer night in (I think) 1962 my brother and I convinced them to take us to the drive-in to see the Marlon Brando version of “Mutiny on the Bounty.” As I recall, the co-feature was “Tarzan’s Greatest Adventure.” When I grew up, I saw lots of movies at drive-ins and though that particular combination may not have been the worst pairing, it was certainly one of the oddest. Two movies with absolutely nothing in common.
I watched drive in movies in WI until at least the late 70s. Arizona had a theater that was open (IIRC) well past 2000. There are still a few drive in theaters open to this day.
As for the OP, the worst paring was sadly only anecdotal, so I cannot validate it: a friend said he went to a multi-screen drive in and on one of the other screens was a hard X film. It was his first, ah, exposure to X-rated films. He was suitably impressed, so much he doesn;t remember what film the family went to actually see..
I remember my mom taking us to a drive-in double feature of some kid-movie we kids wanted to see, plus “Bob and Carol and Ted and Alice”, which was definitely NOT a kids movie. But the drive-in showed “Bob et al” first! We kids weren’t following it, and my mom told us maybe we should nap before “our” movie came on. So now all us kids were sleepy during the G-rated movie, so I don’t even remember what the movie was. I just remember being robbed of our movie by Bob and Carol and Ted and Alice.
I don’t remember any double features. I remember seeing Jaws, Smokey and the Bandit, Schick Sunn Classics The Mysterious Monsters and Search for Noah’s Ark. I remember a similar situation as someone else noted where we went to see Disney’s The Boatniks (a re-release) and the other screen was showing Happy Hooker Goes to Washington, so my 8 year old self spent most of the movie looking at the rear view mirror and the other movie.
By the way, that drive-in is still open to this day.
My parents took me and my sister to “The Bridge At Remagen”, a gritty World War 2 movie (Dad had served, and wanted to instill violent patriotism in us). The first half of the double bill was “If It’s Tuesday, This Must Be Belgium”.
Mom still laughs at how she was worried about her kids seeing the war movie, but the comedy was the one that had people jumping into bed with each other.
Our town still has a drive-in and it isn’t uncommon for a kids movie to open for something rated R. I specifically remember going to see Mr. Peabody & Sherman with the quite violent Lucy.
17-year-old me really wanted to see Midnight Cowboy, but it was the second feature. My buddies and I had to leave shortly after it started, because curfew.
I’ve only seen one double feature, so it qualifies as “worst” (as well as “best”, of course). It was at a drive-in; the twilight feature was Spies Like Us and the nightcap was Top Gun.
The juxtaposition of a Cold War comedy with a Cold War rah-rah war movie was pretty jarring.
I seem to recall “Soylent Green,” a sci-fi movie about a dystopian future, teamed with “Lolly Madonna,” a movie about demented hillbillies in a dystopian present.