10 Most Entertaining Managers in World Football History

What makes a manager entertaining? Several things, really.

A sense of humor is a good start, for sure. But a complete lack thereof can be just as entertaining.

Winning helps, but losing is also a whole lot of fun for the haters.

A general unwillingness to listen to reason? Yeah, that's always entertaining. So are scathing comments, paranoia, myopia and unbridled anger.

You'll find all those in this list of football's 10 most entertaining managers of all time.

10. Claude Anelka

Teams managed—Raith Rovers, AC St. Louis

After years of engineering transfers for his brother, Nicolas Anelka, Claude decided he would become a manager in 2004.

He offered £300,000 to any lower-league club that would give him a chance as manager. Raith Rovers of Scotland gave him his shot.

The Guardian sums up his tenure best.

"Citing Cruyff, Wenger and the boss of Chinawhite nightclub as influences, his philosophy and signings—some from the Paris seven-a-side leagues—brought Rovers just one point from 24 before he stepped aside.

For some reason, AC St. Louis, an American club that lasted all of two years, hired him in 2010. The club dissolved a year later.

9. Sir Bobby Robson

Teams managed—Fulham, Ipswich Town, England, PSV Eindhoven (twice), Sporting CP, Porto, Barcelona, Newcastle United

Sir Bobby Robson was a great player and manager who had the ability to say some really funny stuff.

Check out these quotes, some of which I've included below.

"The first 90 minutes are the most important."

"We’re flying on the Concorde. That’ll shorten the distance—that’s self-explanatory."

"There will be a game where somebody scores more than Brazil and that might be the game they lose."

8. Ruud Gullit

Teams managed—Chelsea, Newcastle United, Feyenoord, Los Angeles Galaxy, Terek Grozny

Ruud Gullit was a heck of a player. As a manager, he's terrible.

At Chelsea, he couldn't get along with his chairman, who was indeed crazy.

At Newcastle, he benched Alan Shearer, who was probably England's best striker at the time.

In Los Angeles, he lost the confidence of his entire locker room after dissing them in a big way.

In Russia, with Terek Grozny, he got fired for being more interested in partying than coaching.

7. Hristo Stoichkov

Teams managed—Bulgaria, Celta Vigo, Mamelodi Sundowns

Near the end of a brilliant playing career, Hristo Stoichkov broke the leg of a college player during a friendly match.

He took that same scorched Earth policy with him to the managerial ranks.

His first job was with Bulgaria, his home country. His temper quickly led to two veterans quitting the team.

Later, the captain said he wouldn't play as long as Stoichkov was manager.

At Celta Vigo in Spain, he famously said, "I don't believe in tactics." That much was apparent when he started one match with Bulgaria in a 2-4-4 formation.

Stoichkov is entertaining for being so very, very bad. And crazy.

6. Brian Clough

Teams managed—Hartlepool United, Derby County, Brighton & Hove Albion, Leeds United, Nottingham Forest

Brian Clough was Arsene Wenger before there was Arsene Wenger. He was Moneyball before there was Moneyball.

Clough made a career out of finding old or castoff players for cheap, getting the most out of them and winning titles with them.

He was also outspoken, controversial and downright hilarious.

Check out some quotes here, two of which I've included below.

"I wouldn't say I was the best manager in the business. But I was in the top one."

"For all his horses, knighthoods and championships, he hasn't got two of what I've got. And I don't mean balls"—referring to Sir Alex Ferguson's failure to win two successive European Cups.

5. Jose Mourinho

Teams managed—Benfica, U.D. Leiria, Porto, Chelsea, Inter, Real Madrid

First, he declared himself "The Special One." Then, he took it back.

But how can he be "The Special One?" According to one referee, he's an "enemy of football."

He once called Arsenal manager Arsene Wenger a "voyeur."

In an illustrious career of smack talking, he's also called Barcelona a small club and turned heads with a variety of other comments.

If Mourinho continues this form, this could truly be a career for the ages.

4. Arsene Wenger

Teams managed—Nancy-Lorraine, AS Monaco, Nagoya Grampus Eight, Arsenal

Arsene Wenger strives to cultivate a sophisticated, urbane, intellectual image as a manager.

But sometimes, it's just not so.

He got himself sent off during a match against Manchester United last term—and promptly took to the stands to plead his cause.

He also threw the water bottle that one time.

He almost threw down with Martin Jol (who, seriously, would have won that fight easily).

He refused to shake hands with Alan Pardew.

He pushed a referee.

And there's everyone's favorite: "I did not see the incident."

Good times all around.

3. Sir Alex Ferguson

Teams managed—East Stirlingshire, St. Mirren, Aberdeen, Scotland, Manchester United

Love him or hate him, Sir Alex Ferguson always keeps things interesting.

Remember that Kevin Keegan rant back in the 90s?

That was the result of Fergie's famous mind games. You could argue it won Manchester United the title that year.

Ferguson also has a fractious relationship with referees, a fact that's led to several suspensions.

He's feuded with BBC and UEFA (see April 5, 2003).

He even managed to besmirch David Beckham's pretty little face (see the first entry under 2003).

Combine all that with his reputation as a poor loser and a hothead in the locker room, and you've got a unique, entertaining personality.

2. Kevin Keegan

Teams managed—Newcastle United (twice), Fulham, England, Manchester City

Author of perhaps the most famous managerial meltdown in modern football history, Kevin Keegan is the king of football malapropisms.

That's a fancy word for saying stupid things. Imagine a combination of George W. Bush and Les Miles.

Here is a sampling.

"I'm not disappointed, just disappointed."

"It's like a toaster, the ref's shirt pocket. Every time there's a tackle, up pops a yellow card."

"They compare Steve McManaman to Steve Heighway and he's nothing like him, but I can see why—it's because he's a bit different."

"Chile have three options—they could win or they could lose."

"Argentina won't be at Euro 2000 because they're from South America."

And my personal favorite: "They're the second best team in the world and there's no higher praise than that."

1. Diego Maradona

Teams managed: Textil Mandiyú, Racing Club de Avellaneda, Argentina, Al Wasl

Maradona would be No. 1 if this had been the only thing he'd ever said as a manager:

"

To those who did not believe: now suck my d**k - I'm sorry ladies for my words - and keep on sucking it. I am either white or black. I will never be grey in my life. You treated me as you did. Now keep on sucking d**ks. I am grateful to my players and to the Argentinian people. I thank no one but them. The rest, keep on sucking d**ks.

"

He said that after qualifying for the 2010 World Cup as Argentina's manager. Alas, that's not the only entertaining thing Maradona has said or done.

He gained a bunch of weight. He lost a lot of weight.

He's battled drug addiction.

He had his earrings seized after longstanding financial problems.

In other words, there's never a dull moment with Diego around. Never.