NHL Power Rankings: 22 Wackiest Personalities in NHL History

These men have fought with fans, regretted shaking hands and driven players into the playing surface.

They are usually enforcers.

There is a goalie that fought a defensemen, a player that fought a fan and a playboy that fought anti-homosexuality.

Some are warmly received in hockey circles. Others will always be remembered for their antics.

Hockey is full of characters.

The following are The NHL's 22 Wackiest Personalities of All Time.

Honorable Mention: Esa Tikkanen

Shout out to Pekka (see comment below) for bringing this Esa Tikkanen up.

He definitely was in a world of his own.

22. Wayne Maki

In a preseason game on September 21, 1969, while playing for the St. Louis Blues, Maki engaged in a stick-swinging fight with “Terrible” Ted Green of the Boston Bruins.

Maki struck Green in the head, causing a fractured skull and brain injury.

The Canucks would pick up Maki in the 1970 Expansion Draft. He would lead the team in scoring in his first two years with the team.

21. George Parros

The Princeton-educated enforcer from Washington, Pennsylvania, Parros is known more for his ‘stache than his character, but can also talk the talk.

He can be followed on Twitter (@Stache16).

20. Derek Boogaard

The hockey world suffered a terrible loss on May 13 when Boogaard was found dead in his Minneapolis apartment.

The Boogeyman, who stood 6'7" and weighted 265 pounds, was considered one of the most intimidating fighters in the NHL.

19. Mike Milbury

Currently an analyst for NESN, Hockey Night in Canada and NBC, Milbury had a distinguished career with the Boston Bruins as a player (1974-89), head coach and GM.

He also served as head coach and GM of the New York Islanders. While with the Islanders, he was the guy who shipped off Roberto Luongo in favor of Rick DiPietro.

However, he is probably best remembered for the brawl he had as a member of the Bruins.

On December 23, 1979, following a 4-3 victory over the Rangers in Madison Square Garden, Milbury and teammates Terry O’Reilly, Peter McNab and Stan Jonathan engaged in a fight with the Blueshirt supporters after one fan cut Jonathan in the face.

The incident would lead to the raising of the Plexiglas in arenas around the league.

18. Brad May

Considered a premier pugilist in the league, May played over 1,000 games as a journeyman enforcer.
He is remembered for three incidents:

1) As a member of the Phoenix Coyotes in 2000, he was suspended 20 games for slashing Columbus Blue Jackets forward Steve Heize in the nose with his stick.

Two years later he was arrested for assaulting a police officer outside a Scottsdale nightclub.

2) He put the bounty on the head of Steve Moore of the Colorado Avalanche, who was viciously attacked by Todd Bertuzzi.

3) He sucker-punched Kim Johansson of the Minnesota Wild during Game 4 in the first round of the 2007 Stanley Cup Playoffs.

17. Darren McCarty

A winner of four Stanley Cups in Detroit (the 2008 victory came after a career resurrection), McCarty is one of the most notorious enforcers during the Red Wings-Avalanche rivalry.

He is best remembered for his actions during the Fight Night at the Joe.

On March 26, 1997, a giant brawl broke out in a Detroit-Colorado contest. McCarty squared off with Colorado’s most notorious enforcer, Claude Lemieux and cleaned his clock.

Later in the contest he netted the game-winner.

His actions are said to have broken Detroit’s 40-year Stanley Cup curse.

16. Tony Granato

Granato has served as the head coach of the Avalanche and was awarded the Bill Masterson Trophy in 1997, but he may be most remembered for slashing Chicago's Neil Wilkinson as a member of the Los Angeles Kings in 1994.

The action merited a 15-game suspension.

15. Tony Twist

A premier enforcer in NHL history, Twist had two memorable stints with the St. Louis Blues before injuring his pelvis in a motorcycling accident in 1999.

Twist gained great enough notoriety in his short career (he was drafted in 1989) to have a Todd McFarlane character mob enforcer character named after him.

Antonio “Tony Twist” Twistelli was popular in the Spawn comics, but unpopular in Twist’s book.

He sued the company for profiting from his likeness.

14. Jim Playfair

Former head coach of the Calgary Flames and currently the head coach of their minor league team, Abbotsford Heat, in the AHL Playfair is remembered for his stick-breaking incident while coaching the Heat.

On March 27, 2010, Playfair broke two hockey sticks and ripped off his jacket in protest (see the assistant coach in the background kindly remove it for him) of a controversial call.

The video has been viewed half a million times on YouTube.

13. Ray Emery

A boxing fanatic that has been nicknamed Sugar Ray, Emery has been the center of controversy during his tenure in the NHL.

As a minor leaguer, he tried his hand at fighting... by taking on a defensemen.

He was signed by Chicago in the offseason.

12. Dino Ciccarelli

Elected to the Hall of Fame in 2010, Ciccarelli's 608 career goals are most by an undrafted player in NHL history.

Ciccarelli will most be remembered, however, for his antics on and off the ice:

1) In 1987 he pleaded guilty to indecent exposure and received probation.

2) On January 6, 1988, in a game played at Maple Leaf Gardens, Ciccarelli attacked then-Maple Leafs rookie defenseman Luke Richardson with his stick.

3) As a member of the Red Wings in 1996, he famously told reporters he was upset with shaking the Avalanche's Claude Lemieux's hand after a playoff series between the two teams.

11. Patrick Roy

Considered by experts as one of the best goaltenders of all-time, Roy was not shy to leave the net from time to time.

During the Avalanche-Red Wings rivalry at the turn of the century, Roy would fight two Detroit goaltenders: Mike Vernon and Chris Osgood.

His fight with Osgood is remembered as one of the greatest goalie fights in the history of the NHL.

10. Theoren Fleury

Theo Fleury, a small and chippy forward who played primarily for the Calgary Flames, will be remembered for many things:

1) In 1987, the year he was drafted in the eighth round by the Flames, he was in the middle of the Punch-up in Piestany, a brawl that led to the disqualification of both Canada and the Soviet Union in the World Junior Championships.

2) Overcoming drug and alcohol addictions that forced him into retirement from hockey in 2003.

3) An unsuccessful comeback in 2009.

4) Filming a pilot for a reality show.

5) His book, Playing with Fire, which made allegations that he was sexually abused by his former coach, Graham Jones.

9. Terry O'Reilly

O’Reilly joined Milbury in the Madison Square Garden brawl in 1979.

He is the player Adam Sandler based his Happy Gilmore character on.

Enough said.

8. Marty McSorley

Known as Wayne Gretzky's primary enforcer throughout his tenure in the NHL, McSorley has tried his hand in coaching and acting as well.

He may be best remembered, however, for swinging his stick and hitting Donald Brashear in the head with three seconds left in a February 21, 2000, contest.

Brashear, a feared enforcer, suffered a Grade 3 concussion.

On October 4, 2000, he pleaded guilty to assault with a weapon and got 18 months probation.
He suffered a year-long NHL suspension that ended his career.

7. Todd Bertuzzi

Although he has been a prolific scorer throughout his career, Bertuzzi will go down as the man who took retaliation to the next level when he pile-drove Colorado’s Matt Moore as a member of the Vancouver Canucks.

It was an overreaction to a hit Moore laid on legendary Vancouver captain Markus Naslund.

6. Claude Limieux

A journeyman enforcer, Lemieux established a reputation as one of the league's dirtiest players. An ESPN special listed him as No. 2 in the "The Top 10 Most Hated NHL Players of All Time."

1) In a playoff game against the Calgary Flames, Lemieux, a member of the Montreal Canadiens, bit Calgary's Jim Peplinski on the finger during a scuffle.

2) In 1996, as a member of the Colorado Avalance, Lemieux checked Kris Draper of the Detroit Red Wings into the boards from behind during a playoff series. Draper suffered a concussion, broken jaw, broken nose and broken cheekbone.

3) This led to bad blood between the two teams, which reached fever pitch the next season. During a fight in the infamous Red Wings-Avalanche brawl, Wings enforcer Darren McCarty dropped Lemieux with a right hook to the face.

This led to the Patrick Roy-Chris Osgood goalie fight.

5. Sean Avery

The only player rated higher on ESPN’s Most Hated Player List was Sean Avery.

He has had many egregious infractions, which include his notorious dive as a member of the LA Kings and waving his stick ferociously in front of legendary Devils goaltender Martin Brodeur on a power play (which led to the “Sean Avery Rule”).

However, Avery’s “sloppy seconds” comment will probably be placed on his epitaph.

Preceding a December 2, 2008, contest in Calgary, Avery had this to say about Dion Phaneuf (then of the Flames), who was dating his former girlfriend Elisha Cuthbert:

“I'm just going to say one thing. I'm really happy to be back in Calgary; I love Canada. I just want to comment on how it's become like a common thing in the NHL for guys to fall in love with my sloppy seconds. I don't know what that's about, but enjoy the game tonight.”

4. Dave Hanson

Although he played 33 games in the NHL, Hanson will be best remembered as a member of the Hanson Brother in the 1977 hit Slap Shot.

3. Don Cherry

Cherry played a single NHL game for the Boston Bruins and coached the team during the Bobby Orr days and currently works for CBC Television.

However, the patriotic Canadian will be remembered more for his actions away from the ice.

There are many. Here are my top three:

3) In 1989, he referred to Finnish-born Winnipeg Jets Assistant Coach Alpo Suhonen as "some kind of dog food."

2) A staunch supporter of “old time hockey,” in 2004 he claimed that players who wore visors were not masculine and usually European or French.

1) Frequently seen wearing pink, in 2010 Cherry was quoted expressing his dislike for “left-wing, anti-pinko newspapers” that “rip him to shreds.”

2. Tie Domi

This fool got in a fight with a fan.

1. Mike Danton

The only thing that tops that…

a player hiring a hit man.