Spirit of Speed 1937
There's a racing mission in Gathering of Developers' original Mafia set in 1932, and it's the cause of one of those frustrating difficulty spikes that make players give up on a game. Racecars from the 1930s didn't handle great, and aren't that much fun to drive. Spirit of Speed 1937 is that one annoying level if it was an entire game, but beset by even more problems than just being set in an era when racing cars steered like bulls. It was single-player only, the Dreamcast version had painfully long load times, and some of the cars were so slow they could never win a race – tellingly the computer never chose them – and were entirely pointless except as newbie traps. On the upside it made people appreciate the race in Mafia for only being one mission.