I always loved the story of the "three-sided" Monty Python record, where the B side had two parallel concentric grooves, causing different tracks to play depending on where the needle was dropped. I always wondered what kind of equipment went into producing it.

Monty Python’s Matching Tie and Handkerchief Executive Version.

From what I know about record manufacturing, creating the lacquer master would involve adjusting the angle of the groove to allow for two concentric grooves to be laid, along with some care in creating that master. But once it’s done, the manufacturing process is handled through a stamping process (so a vinyl record isn’t cut, it’s pressed with a metal die that’s created from the lacquer master through electroplating).

The same goes for the 1994 first pressing of Marillion's Brave.

Side 4 has a double groove, which would give you either The Great Escape + Made again (a sort of a happy ending) or The Great Escape + 20 minutes of water sounds (which can be interpreted as the sad ending).

Reference: https://en.wikipedia.org/wiki/Brave_(Marillion_album)#Vinyl_... (I also have a copy and can confirm indeed it works like that).

De La Soul's 12" Single for "Me Myself And I" also has its second side cut with two grooves. The hype sticker says, "3 Sides." Each time you put the needle down you have a 50/50 chance to hear the song you're trying to hear. :-)

https://www.discogs.com/master/19554-De-La-Soul-Me-Myself-An...

I bought a Record Store Day release of Ella Fitzgerald live in Berlin that did this around 2020. Very cool stuff.

Jack White did something similar with Lazaretto.