
8 riders!
This book (Bicycles and Tricycles, by Sharp) was published in 1896, so the disk wheels were around by then, or earlier?

Amphibibious! (That's a classic movie reference, not a typo)
Bolted together (& disassembleable) aluminum frame with octagonal tubing, 1930s - before Loctite was invented. What could possibly go wrong?
Quad tandem, the hard way.
Watch out for low overpasses.
Jocelyn Lovell, on a bike he made himself. The gears on each side had different ratios, a lower one for the first 70 m, and a higher one for the rest of the race (a 1 km time trial, aka "kilo") He rode it at World Championships but didn't win, and it never became popular.