This one is a classic:
A 1960 Sportsman Race at Daytona. A massive 68-car field, with Banjo Mathews, Fireball Roberts, etc, and I think that's a 1959 Cadillac Convertible Pace Car. At 1:54 into this highlight reel, there's a massive 37-car pileup (the largest wreck in history). Everyone walked away, but the carnage was incredible.
https://www.youtube.com/watch?v=5Eb3Sf6Kf1I
Some of you may enjoy watching this whole 3:23 film. Lots of real oddball cars on the track, and I swear I catch a glimpse of a Studebaker.