Alistair Overeem: 5 Defining Moments

The date was Oct. 24, 1999. “Fight Club” was enjoying its second week in theaters; Santana’s “Smooth” was No. 1 on the Billboard Hot 100 list; and a 19-year-old Dutchman entered the professional MMA arena for the first time in Haarlem, Netherlands. His name was Alistair Overeem.

Over the next 16-plus years, Overeem established himself as a dominant force in mixed martial arts with world-class kickboxing skills and an underrated submission game, first at 205 pounds and then as a heavyweight. The 2010 K-1 World Grand Prix winner had a 14-fight run in Pride Fighting Championships, captured titles in Dream and Strikeforce and cemented his reputation as one of the sport’s premier finishers. Of his 41 career victories, 37 have come by knockout, technical knockout or submission, a staggering 31 of them inside one round. Overeem arrived in the Ultimate Fighting Championship in 2011 and, despite some high-profile hiccups, has posted a respectable 6-3 record in the Octagon. A current four-fight winning streak made him the No. 1 contender for the heavyweight championship, a title for which he will challenge reigning champion Stipe Miocic in the UFC 203 (current odds) headliner on Saturday in Cleveland.

In a career full of defining moments, here are five that stand out:

1. Retiring Lesnar

It took less than half a round with Overeem for Brock Lesnar to lose all taste for battle. “The Demolition Man” softened Lesnar with knees to the gut and finished him with a brutal liver kick in the UFC 141 main event on Dec. 30, 2011 at the MGM Grand Garden Arena in Las Vegas, forcing the stoppage 2:26 into round one. “Today was all about bad intentions. First or second round -- I promised,” Overeem said. “Nice little K-1 body kick. I trained the takedown defense a lot. Brock is an excellent wrestler, so I had to step up my game.” Lesnar attempted one single-leg takedown and was turned away by the hulking Dutchman, who showed no regard for the former World Wrestling Entertainment superstar’s skills. He walked through Lesnar’s punches, bullied his way into the clinch and fired off the crushing knees for which he has become feared. Lesnar slowly wilted. Unable to get the fight the ground, Lesnar ate one last kick to the abdomen and crumpled at the base of the cage. There, Overeem swarmed with punches until referee Mario Yamasaki intervened on the onetime UFC champion’s behalf. Afterward, Lesnar -- who seven months earlier had roughly a foot of his colon removed following a second bout with diverticulitis -- announced his retirement from mixed martial arts. “My hat is off to Alistair Overeem. I’ve had a really difficult couple of years with my disease,” he said. “I’m going to officially say that tonight is the last night you will see me in the Octagon. Brock Lesnar is officially retired. I promised my wife and my kids if I won this fight that I would get a title shot and that would be my last one, but if I lost tonight ... everyone, you’ve been great.” Lesnar resumed his WWE career and remained on the sidelines in MMA for the better part of five years, returning to defeat Mark Hunt at UFC 200.

2. Phenomenal Guillotine

When Vitor Belfort entered his clash with Overeem in the opening round of the 2005 Pride middleweight grand prix, he had never before been submitted. That changed on April 23, 2005, as Overeem dropped a guillotine on the Carlson Gracie-trained Brazilian jiu-jitsu black belt in front of 45,423 fans at the Osaka Dome in Osaka, Japan. He greeted Belfort with some high-octane knees, executed a takedown from the clinch and battered him with hammerfists and punches before exiting an armbar with a soccer kick. Overeem later yielded a takedown to the Brazilian, and while he drew a yellow card for passivity, he avoided meaningful damage on the ground. They were restarted on the feet after another Overeem takedown in the waning moments. The Dutch kickboxer then lit up Belfort with a driving knee and uppercut, forcing him to retreat to the canvas. Soon after, he locked up a guillotine as “The Phenom” attempted to scramble to a more advantageous position, wrapped him in guard and forced the tapout 9:36 into round one. It was the first of six Overeem wins against former, current or future UFC champions. He went on to defeat Belfort in their June 2006 rematch.

3. Hook Shot

Theirs was a showdown years in the making. Overeem disposed of former heavyweight champion Junior dos Santos with second-round punches in the UFC on Fox 17 co-main event on Dec. 19 in Orlando, Florida. He drew the curtain 4:43 into round two and added another signature name to his resume. Dos Santos appeared tentative and unsure of himself, his potent right hand cocked but rarely thrown. Overeem picked his spots. He smashed the Brazilian in the nose with a crushing left hand in what was an otherwise tepid first round and opened multiple cuts, one near the right eye, with a wicked two-punch combination in the second. Outside of a flurry along the fence, dos Santos’ offense was virtually non-existent. Late in the second round, Overeem stepped in with a savage left hook and floored the onetime UFC titleholder. Subsequent hammerfists on the dazed and exposed dos Santos prompted referee Dan Miragliotta to act.

4. Golden Glory

Overeem got his hands on his first piece of major MMA hardware on Nov. 16, 2007, when he laid claim to the inaugural Strikeforce heavyweight championship at the HP Pavilion in San Jose, California. Paul Buentello was the victim. Overeem secured a takedown inside the first 10 seconds, advanced immediately to side control and ripped into the Texan with punches and knees. Buentello worked back to his feet but paid a steep price, as he was met with a series of knees to the body, some of which lifted him off his feet. He survived to see a second round, but his situation did not improve. There, he once again found himself either trapped in the punishing Overeem clinch or on the ground absorbing further damage. Late in the round, the merciless and calculated Dutchman backed Buentello into the fence and unleashed two knees to the solar plexus, the second of which had “The Headhunter” tapping on all fours. The end came a little less than nine minutes into the match.

5. New Year’s Eve Bash

Less than three weeks after he won the 2010 K-1 World Grand Prix, Overeem made an example of heavyweight prospect Todd Duffee. He needed just 19 seconds to blow away the American Top Team rep at K-1 Dynamite 2010 before 26,729 fans at the Saitama Super Arena in Saitama, Japan. Having accepted the bout on short notice, Duffee had a deer-in-head-lights look about him -- and for god reason. Overeem dodged the Evansville, Indiana, native’s initial volley and tore into him with knees to the midsection. One of the blows short-circuited Duffee and left him open to two devastating hooks that connected next. Out went the lights, as Duffee collapsed to a seated position and fell through the ropes. The New Year’s Eve rout provided a fitting end to one of Overeem’s most productive 12-month campaigns. “This year, I won [or defended] three world titles -- Strikeforce, then K-1 and now Dream -- and I promise you all that I’m going to keep giving you great fights.” Consider the promise kept, as wins over Lesnar, dos Santos, Andrei Arlovski, Roy Nelson, Frank Mir and Stefan Struve have followed.