Late to the party, but here's my thought: Duesenberg straight 8, 420 ci, DOHC, 4 valves/cylinder, 265HP in 192-f***ing-8. If that's not enough challenge, it was supercharged in 1932 to 320HP. And if you're feeling masochistic, in 1935 tuned to almost 400HP with a custom dual carb "ram's horn"...