Top 15 'Rich Jerk' Gimmicks in Wrestling History

It was the Wu-Tang Clan that said "Cash rules everything around me." Several of the pro wrestlers in the below list would agree. They've all incorporated being rich into their gimmicks, match types, p

It was the Wu-Tang Clan that said "Cash rules everything around me." Several of the pro wrestlers in the below list would agree. They've all incorporated being rich into their gimmicks, match types, promos, and overall characters. With money on the mind and Tax Day for the United States looming, this is a look at the 15 greatest intersections between money and pro wrestling.

Wrestling has always been a pop culture staple for the less-wealthy throughout its lifetime in America. From the very beginning, rich characters have been easy heels. Most cheap heel heat can come from a bad guy walking out and calling all the paying customers low-class trash from (city name). The history of pro wrestling also features frequent battle royals for cash prizes headlining independent events.

Whether between rich and poor superstars or between employees and employers, there have been countless feuds in wrestling history over money. All of the title belts in the WWE are very shiny gold, and every superstar in the company wants to be champion. Whenever a good guy turns evil to capture the title, he's accused of "selling out." Seth Rollins is still serenaded with "You Sold Out" chants for leaving his Shield brothers to join the Authority. He's the latest in a long line of characters that choose the easy path of rich, powerful backers to make a career leap instead of hard work.

Recently, Brock Lesnar has bragged about getting paid full-time money for part-time work. The Rock and The Undertaker also have a similar contracts - only wrestling at huge events like WrestleMania, if at all. Several other stars have gotten very rich from pro wrestling throughout the years. But this list is relating more to the richest characters that used their money to their advantage on camera and in storylines.

15 Ted DiBiase, Jr


The younger DiBiase just makes the cut almost on name value alone. After his debut and run in Legacy with Cody Rhodes and Randy Orton, Ted Jr. would return to his family roots with a heel turn and run as the Million Dollar Champion. For the majority of 2010, he'd reign with his father's Million Dollar Belt, never defending the unsanctioned title.

After unsuccessfully making R-Truth his Virgil 2.0, Ted Jr. feuded with Goldust over the belt until it was stolen and returned to his father. It was only the briefest of flashes that Ted Jr. would follow in his father's footsteps.

14 M.V.P.


M.V.P. entered the WWE with a dynamite gimmick based on arrogant diva NFL free agents like Terrell Owens. Before even entering the ring, he'd have segments flaunting his jewelry, negotiating with General Manager Teddy Long about money, and bragging about being the most coveted free agent in sports. He turned that character and charisma into great in-ring work during US Title matches with Chris Benoit and a near year-long reign as champion.

Despite all this momentum, the WWE would eventually bury him under a losing streak that sapped all energy from the character. Ironically, after his release in 2010, MVP would be a desired free agent, signing with New Japan Pro Wrestling and TNA.

13 The Miz


Since his return in June 2014, The Miz has reinvented himself with a fun arrogant movie star gimmick after filming The Marine 4. In his early matches, he went as far as to avoid any attacks to his face, in fear of ruining his "money-maker." He even acquired a paid lackey, Damien Sandow (later Mizdow), as his "stunt double." The two became WWE Tag Team Champions, but have recently broken up.

The rich movie-star heel has been a great character for The Miz and some of his best work since joining the WWE on the heels of his Real World fame. His current storyline with Mizdow and co-star Summer Rae is one of the highlights of WWE TV in 2015.

12 Terri Runnels Invitational


The TLC matches between The Hardyz, Dudley Boyz, and Edge & Christian are part of wrestling history. However, it's not as well-known that the whole feud and phenomenon started over money. Back in 1999, The Hardyz were the New Brood and neither team had tasted the Tag Team Titles.

But then, Terri Runnels hung $100,000 over the ring, and challenged Edge & Christian and the Hardyz to go get it. The result was the first ladder match between the two teams. Terri's managerial services also hung in the balance. This match at No Mercy for a bag of money was just the prelude for the Wrestlemania Tag Title Triangle Ladder match, and the TLC classics to follow.

11 11, Mean Street Posse


The Mean Street Posse had a brief, but memorable run as lackeys for Shane McMahon. They first showed up ringside wearing sweater vests and dress pants, as they were billed as childhood friends of the owner's son from wealthy Stamford, CT. It wouldn't take long for them to get involved in the action, interfering in Shane's matches for most of 1999 and 2000.

The promos emphasizing the "mean streets of Greenwich" (one of the richest cities in the United States) were a comedy highlight from the Attitude Era. These three guys got nuclear heat from blue-collar fans wanting to see the rich kids get beaten up. They never went far after distancing themselves from Shane.

10 The Ringmaster


Before there was Stone Cold, Austin 3:16, and the Texas Rattlesnake, there was The Ringmaster Steve Austin. Austin's initial run in 1995 was with Ted DiBiase as manager, who awarded him the Million Dollar Title for over 150 days.

The pairing didn't last long, as Austin was unhappy with the gimmick and DiBiase was leaving for WCW shortly, but it still produced a memorable feud with Savio Vega and the seeds for Austin 3:16. His face turn was jump-started by abandoning the Million Dollar Belt and claiming to lose a Ted DiBiase retirement match on purpose.

9 Hunter Hearst Helmsley


HHH was another wrestler that used a turn from a rich-person gimmick to become a huge star. The three H's of Hunter Hearst Helmsley were originally part of his Connecticut blue-blood gimmick in the mid-90s. His finisher, the Pedigree, still keeps the same name from that gimmick after all these years.

While he did win the Intercontinental Title as Hunter, the switch to Triple H and D-X, along with throwing off his rich clothing for jeans and leather jackets is what helped propel him to the top of the WWE, both on and off camera.

8 Shane McMahon


Shane was the leader of the "Mean Street Posse" from an earlier entry, and also spent a good deal of his on-air time as a rich arrogant heel. He's also guaranteed a spot in the list with his awesome theme song, "Here Comes The Money." In addition to wrestling as the company owner's son, Shane would also be the on-screen owner and leader of WCW during the invasion storyline.

The younger McMahon would bounce between hero and villain largely depending on who he was facing at the time, but he was always a wealthy part-timer dipping his toe into the wrestling world.

7 Alberto Del Rio


Del Rio had a great gimmick out of the gate playing a rich Mexican aristocrat. He had several great small touches to make his character stand out - nice clothes, entering in an expensive car, and his own personal hired ring announcer, Ricardo Rodriguez, a servant in the mold of Virgil.

Alberto would stay as his rich heel character for his entire four years in the WWE, minus a brief face turn.

6 The Rock


The Rock's first WWE Championship came in 1998 when he sold out and joined The Corporation. The resulting feud with outcast Mankind led to three great gimmick title matches in 1999:The I Quit match at the Royal Rumble, the Empty Arena match for Super Bowl Halftime, and the Last Man Standing match in February. Some of The Rock's best promo work came from his heelish disdain for Mankind throughout this feud.

The Rock would again be a rich heel in 2003, returning from hiatus and declaring that his movie career was more important than pro wrestling. After backing up his new persona with wins over Hulk Hogan and Stone Cold, real life would follow the storylines one more time when Rocky left WWE for the movies again. With his crossover stardom through the roof, it's unlikely he'll ever be booed again.



Bradshaw was able to rise from the mid-card tag team depths by adopting a rich Texan conservative gimmick that became immensely popular. In addition to his cowboy hat, JBL would come to the ring in a gaudy limo with Texas longhorns on the front. At his height, JBL's "Cabinet" stable would have five members.

JBL backed up the cartoonish parts of his character in the ring with a near year-long reign as WWE Champion. He'd also cement his "rich prick" credentials with a feud with Shawn Michaels, where JBL employed and practically owned the Heartbreak Kid. After retirement, JBL has remained a part of WWE, ruining matches with his commentary for the last three years.

4 I.R.S.


Irwin R. Schyster, better known as I.R.S., had a memorable run as an evil tax man in the cartoonish early 90s. After accusing several other wrestlers of not paying their taxes, he'd achieve more success as one half of Money Inc with Ted DiBiase, winning the tag team titles three times.

Even after the end of that tag team, I.R.S. remained a staple of DiBiase's Million Dollar Corporation until leaving in 1995 following high-profile feuds with Razor Ramon and The Undertaker. Even in WCW, he'd keep parts of his rich man character while wrestling under the name "Mr. Wallstreet."

3 Ric Flair


The original flashy, rich superstar, Ric Flair ends up at the top of almost every list he's in, and this is no exception. His longtime rivalry with Dusty Rhodes was built on his high-class fans wearing suits and being better than Dusty's working-class supporters. As the Four Horseman stable rose and Flair's status along with it, he would refer to himself as a "stylin,' profilin,' jet flying, limousine ridin' son of a gun" constantly.

Even in the later stages of his career, Flair continued to be a rich, stylish heel backer to bad guy groups. He was a big part of Evolution's run and success from 2003-2005. And even in the twilight of his career during a short stint in TNA, he remade the Four Horsemen stable as "Fortune" in 2010.

2 Vince McMahon


As "Mr. McMahon," Vince was the greatest evil authority character in all of wrestling history. He has been abusing his power and money to screw over the little guys for almost 20 years on camera. "You're Fired" became an iconic catchphrase due to the rich owner's ability to fire anyone he wanted.

His daughter, Stephanie, has been a chip off his block in her "Billion Dollar Princess" character in recent years, and son Shane had already made the list. Both on camera and off, the McMahon family represents all of the money and power in the WWE. His "battle of the billionaires" with Donald Trump at WrestleMania 23 was one of his last major storylines before his current semi-retirement as a character.

1 Ted DiBiase


Could it be anyone else? The "Million Dollar Man" built his career out of being the richest jerk on earth. DiBiase stood out among the bad guys with his "everybody's got a price" catchphrase and evil laugh. He was more of a comic book villain brought to life, bribing wrestlers with $100 bills and paying fans to perform demeaning tasks.

He blatantly tried to buy the WWE Title from Hulk Hogan in the 1980s and launched into his most high-profile feud during this pursuit. He'd create his own "Million Dollar Championship" and carry it around for years. The first SummerSlam was promoted as "The Mega Bucks vs the Mega Powers" when he tagged with Andre the Giant against Hogan/Savage.

Despite never becoming the actual champion, DiBiase's legacy will live on as one of the best gimmicks and best bad guys of all time. His character was at least an inspiration, if not directly responsible, for many of the other entries on this list.

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Top 15 'Rich Jerk' Gimmicks in Wrestling History