Even when you win against these awful bosses, you still lose.
Giant Evil Tomato With Laser Mouth Power- McDonald's Treasure Land Adventure (Sega Genesis; 1994)
Huge Ball of People Having Orgy- Castlevania: Symphony of the Night (PSX, Xbox Live Arcade)
Three Tornadoes- Superman Returns (EA Games; all systems)
Disturbing Head With Neck-Fat and Pointy Tongue- NARC (Midway; arcade version)
Big White Monkey With Huge Hammer- Halo 2 (Microsoft; Xbox 360)
Lizard With Magic Baton, a.k.a. The Skedar- Perfect Dark (N64)
Tiara-Wearing Alligator Who Rides Around on a Boat- Donkey Kong Country (SNES)
Giant Floating Monkey Head With Huge Swatting Hands- Star Fox Series (SNES, N64)
Massive Turtle With Open Herpes Sores- Contra III: The Alien Wars (SNES)
Obese Man on Rollerblades With C4- Metal Gear Solid 2: Sons of Liberty (PS2)
Giant Mutated Baby With No Face in a Pit- Half-Life (PC, PS2)
David Arquette/Jamie Kennedy (tie)- ESPN NFL 2K5 (Xbox, PS2)