From Sidney Crosby to Lebron James to David Beckham, there is a lot of money to be made in the world of sports endorsements and sponsorships. It’s no surprise then that manufacturers and athletes are so eager to work together. Companies get a big star or team to advertise their product while the team or player in question gets a big paycheck. Sometimes, however, it can all go terribly wrong.

Oxford United – Wang Laboratories

From 1985 to 1989, English soccer club Oxford United took to the pitch with a sponsor which still gets chuckles today. Wang Laboratories is a legitimate business but the 10-year old in all of us can’t stop snickering when we see grown men wearing jerseys emblazoned with ‘Wang’ across the front. Yes, we here at The Richest know it’s immature but be forewarned, there are more to come.

Atletico Madrid – Columbia Pictures

Having a big American movie company sponsor your team is good, right? Spanish side Atletico Madrid may disagree with you on that one. From 2003 to 2005, advertisement on the jerseys constantly changed to include films like Bewitched, Big Fish, Hellboy, Spanglish, Resident Evil 2: Apocalypse, Hitch and XXX.

Ray Lewis - Snuggie

Have you ever seen footage of a lion taking down a gazelle? That was pretty much what Ray Lewis used to do to quarterbacks in the NFL. Now, instead of leaving grown men in tears on the field, Lewis is leaving us in tears of laughter as the former tough-man has his own Snuggie line. That said, he does look pretty comfy.

Mike Ditka, Jim McMahon, William Perry and Denis Rodman – Silestone

What do four Chicago sports personalities and a stone counter-top manufacturer have in common? A very strange 2005 commercial. After Ditka, McMahon and Perry have repeated the phrase “I am Diana Pearl,” – in reference to a color of granite - several times, the camera closes in on Rodman in a bathtub full of bubbles. Funny? Yes. Mildly disturbing? Yes.

Jimmy Johnson – Extenze

Jimmy Johnson will be remembered as a great NFL coach who led the Dallas Cowboys to two Super Bowl Championships. Jimmy Johnson will also be remembered as the spokesman for Extenze, a pill to help ‘that’ part of the body. There is no scientific proof to support Extenze’s claims, but there will always be internet videos of Johnson pushing these pills.

St. Johnstone FC – Bonar Textiles

Since we are on the topic, let’s stay there. St. Johnstone FC is a professional Scottish football club from Perth. They were sponsored by Bonar Textiles from 1991-1998. Written on the front of their jerseys during this period was the word ‘Bonar.’ We warned you there were more to come.

Danish National Team – DONG Energy

OK, last one, we promise. The Danish national men’s team is sponsored by Danish Oil and Natural Gas – the acronym is DONG. To remind people of this company’s generous funding of the national side, much of the team’s apparel and training gear is adorned with DONG. From the above picture, it now looks like there are no more ‘shirts and skins’ practices, replaced instead by ‘shirts and DONGs.’

Pat Jennings – Unipart Oil Filters

Pat Jennings was a pretty good goalkeeper who played in England from 1963 to 1986. While playing for Watford, Tottenham and Arsenal in England he won two FA Cups, two League Cups and a UEFA Cup. So what do you do with a keeper of Jennings’ standing? You dress him up as an oil filter and make him stop shots for your car parts ad. It’s funny and humiliating at the same time.

Tom Brady – UGG

No one can dispute that Tom Brady is a successful and established NFL quarterback. Where we get concerned is with some of the outfits and hair styles he has sported over the years. Yes, UGGs are for men and women but in North America they have been largely claimed by the female market. That is why we snicker at you Tom. Well, Eli Manning actually snickers for a whole other reason, but still.

Neymar – Lupo Underwear

There’s nothing new about athletes in underwear ads. Brazilian soccer sensation Neymar created a bit of a stir with a recent underwear commercial for Lupo. The ad has Neymar dancing in front of ladies when they inquire about his underwear. However, when a man comes in and asks, the Brazilian forward gets concerned and sneaks out of the store. Needless to say, the Brazilian Gay and Lesbian community were less than impressed.

FC Nurnberg – Mister Lady

From 2004 to 2008, Bundesliga side FC Nurnberg were sponsored by a teenage clothing chain. Not a problem, right? Across the front of the jerseys was the company name, ‘Mister Lady.’ If Nurnberg players were trying to strike fear into their opponents and intimidate other teams on the pitch, the sponsorship could not have helped.

Carson Palmer – John Morrell hotdogs

“Who’s ready for a smoked sausage?” Apparently NFL quarterback Carson Palmer. All we can say is that Palmer better have fired his agent after this. Innuendo aside, no good can come by putting a pro-athlete in a hotdog ad.

Akinori Otsuka- Corky’s Pest Control

Japanese pitcher Akinori Otsuka had a brief MLB career between 2004 and 2007. Depsite such a short spell in the big leagues, the ex-Texas Ranger and San Diego Padre found the time to endorse Corky’s Pest Control. The scenes of Otsuka beating CGI ants with a baseball bat and then dancing with the exterminators made for a very bizarre ad.

Jake Delhomme and Steve Smith – Bojangles

When they were playing for the Carolina Panthers, Jake Delhomme and Steve Smith stayed clear of the hotdogs and took part in a funny but strange commercial for chicken chain Bojangles. The two blow up buildings with explosive footballs and make their getaway in a General Lee-style car adorned with a chicken head and tail. You can’t make this stuff up.

AC Milan – Pooh Jeans

AC Milan are a great European soccer team with a great history. They also had one of the greatest sponsorship-related jokes for the 1981-1982 season. Pooh Jeans may be a real brand, but when Milan decided to have ‘Pooh’ labeled across the front of their jerseys, it made a lot of people take notice.

Charles Barkley – Weight Watchers

Ex-NBA player and television commentator Charles Barkley became a spokesperson for Weight Watchers in 2011. Beyond being caught criticizing the company during on-air commentary, people were treated to the 6 foot 6 inch, 250 lbs forward dressed as a women in one of Weight Watcher’s ads. Some things can not be unseen.

Alexander Ovechkin – Eastern Motors

The Russian-born hockey player is best known as a left winger who plays for the Washington Capitals. What is not so well known is Ovechkin's ad for East coast car dealer Eastern Motors during which he tries to sing the company jingle, dances and asks for vodka. It looks like a potential train-wreck but is amusing at the same time.

Ronaldinho – Sex Free Condoms

Soccer legend Ronaldinho has his own line of condoms. What a strange endorsement deal. What a strange name for condoms. Are consumers really going to trust a condom whose spokesperson made a career of slipping one past the keeper on a regular basis?

Joe Nasmith – Hanes Beautymist Pantyhose

Famous for his fur coats, NFL legend quarterback Joe Nasmith caught a lot of people off guard when he endorsed pantyhose. In the ad itself, many thought the legs were a woman’s until the camera scrolled up to Nasmith, smiling and laughing away while holding a box of pantyhose. Funny by today’s standards, it caught a lot of people off guard in the 1970s.

Cristiano Ronaldo – Kentucky Fried Chicken

When you think of professional athletes and peak physical conditioning, what do you think of? Cristiano Ronaldo thinks of KFC. In the Malaysian ad, the Real Madrid star charges through a team of players and then puts a freekick in the net. He proceeds to celebrate with a bucket of KFC. All this time you thought vegetables and exercise were the way to rock hard abs and a world renowned free-kick technique.