6. B.J. Penn
One of the most talented fighters in MMA history finishes sixth on this list. Penn had very good wrestling, outstanding takedown defense and superlative BJJ in his heyday, but he was most impressive and unique for developing excellent striking as well, particularly his sharp, technical, fast and powerful boxing. It was a seemingly unbeatable combination, and only the very greatest wrestlers in the sport, who were bigger than Penn to boot, like Georges St. Pierre, could take advantage. Of course, eventually the evolution lightweight, which has always been one of MMA's most skilled, cutting-edge divisions, caught up with him, but that occurred in 2010, beyond the purview of this list.
In his prime, Penn was truly “The Prodigy” and widely considered the greatest pound-for-pound fighter in the sport. His first pro fight occurred in May 2001 and he immediately made a splash, taking slightly over half a round to knock out highly skilled Din Thomas before recording a timeless 11-second knockout of Caol Uno. However, an early crack at the lightweight crown was unsuccessful, as Penn lost by majority decision to Jens Pulver. When Pulver left the UFC over pay, Penn entered a de facto four-man tournament to crown a new champion. He earned a decision win over Matt Serra, then faced Uno in a rematch for the vacant title. That fight, at UFC 41 in February of 2003, ended in a draw, leaving the division without a champion, which would remain the case for nearly four years.
Next, Penn submitted former Shooto and future Pride lightweight champ Takanori Gomi in Rumble on the Rock, then returned to the UFC and went up to welterweight to challenge previous entry Matt Hughes, one of the best pound-for-pound champions in the sport. To everyone's shock, Penn submitted him in the first round. Penn then left the UFC once again, submitting Duane Ludwig and defeating Renzo Gracie while losing a decision to much larger future UFC light heavyweight champion Lyoto Machida, whom I included on my own list for this decade, during which he was undefeated. When Penn returned to the UFC, he lost a controversial split decision to Georges St. Pierre at welterweight and then lost a rematch against Matt Hughes where he was dominating early but gassed out, being stopped in the third.
The knock on Penn at this point was that despite all his talent, he was prone to occasional lacks of effort and concentration. All that changed in 2007, when Penn gained a new focus and recorded five straight great wins at lightweight, punctuated only by another loss to St. Pierre at welterweight. After gaining revenge against Pulver via submission, Penn choked out Joe Stevenson for the vacant UFC lightweight belt, knocked out tough former champ Sean Sherk, decimated and choked out Kenny Florian and finally, utterly destroyed Diego Sanchez before the doctor mercifully stopped it. All of these fights were one-sided beatings. Thus, by the end of the 2000s, Penn was at his peak, a superb champion and one of the pound-for-pound best in the sport. While the 2010s were often depressing for him, don't let it distract you from his greatness during the previous decade.
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