Chuck Liddell
Liddell was one of the UFC’s first superstars and helped catapult MMA into the mainstream. The Iceman had a brutal style that saw him knock out many opponents. But his career came to an end after a miserable losing streak that saw him absorb a lot of punishment. In the end, UFC President Dana White refused to book him again because of the risk.

However, Liddell couldn’t resist the chance to fight again. Oscar De La Hoya booked Liddell to fight his old rival, Tito Ortiz. But Liddell was almost 50 at the time and couldn’t hang with his younger rival. He lost in the first round and made everybody feel sad in the process. This was one of those freak shows that left a bitter taste (via MMA Fighting).