The 10 Best Matches Of Carlito's Career
John Castro The son of the Puerto Rican wrestling legend Carlos Colón, Carlito -- or Carlito Caribbean Cool as he was first called -- made his WWE debut in 2004, and stuck around the company for six years before his release in 2010. Strictly a midcarder, Carlito is best remembered for using an apple as a prop and his convoluted catchphrase, “I spit in the face of people who don’t want to be cool.”
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While some might remember his talk show Carlito’s Cabana more than any match, Carlito was actually a talented wrestler who put on some good bouts during his time with the company. Without further ado, let’s take a look back at 10 Carlito matches that are totally cool.
10 Carlito vs. John Cena (SmackDown, 10/5/2004)
Carlito certainly has one of the most auspicious debuts of anybody in WWE history, as he beat John Cena for a championship in Cena’s “hometown” (kind of) of Boston. Cena had just completed a Best of Five series with Booker T to win the United States Title, only to be dethroned days later by Carlito. The match is mostly Cena dominating Carlito until the latter can take advantage by hitting Cena with his own chain, but the surprise ending makes it all worth it.
9 Carlito vs. Chris Jericho vs. CM Punk vs. John Morrison vs. Montel Vontavious Porter vs. Mr. Kennedy vs. Shelton Benjamin (WrestleMania 24, 3/30/2008)
Before the Money in the Bank ladder match had its own devoted pay-per-view, the bout was a staple of WrestleMania, and Carlito took part in the fifth-ever MITB match in WWE history. This short but sweet 14-minute match features lots of fun ladder spots and would ultimately end with CM Punk winning the briefcase and getting a push from it. But over the course of the match, every participant would get a cool little spotlight, including Carlito who managed to perform a backstabber on Chris Jericho off of a ladder.
8 Carlito vs. Randy Orton (Unforgiven, 9/17/2006)
When these two men met at Unforgiven 2006, Randy Orton was a young hotshot who had already become the youngest WWE Champion in history, while Carlito was a midcard heel who turned face. As a result, this underrated bout has Carlito wrestling in a way fans hadn’t really seen before, delivering high-flying babyface offense against Orton.
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All of Carlito’s flips and flops would prove to set up an incredible mid-air RKO that ranks among some of Orton’s best, like the ones he did on Seth Rollins and Evan Bourne.
7 Carlito & Primo vs. John Morrison & The Miz (SmackDown, 1/23/2009)
Before Carlito’s brother Primo and cousin Epico were a tag team, Carlito teamed with his brother as the underrated tag duo The Colons and became WWE Tag Team Champions for SmackDown. On an early 2009 SmackDown, the brothers took Raw’s World Tag Team Champions John Morrison and The Miz in a surprisingly awesome non-title sprint. Miz and Morrison would score the win that evening, but The Colons would be the ones to unify the belts in a lumberjack dark match months down the line at WrestleMania 25.
6 Carlito vs. Shelton Benjamin (Vengeance 2005, 6/26/2005)
On the Raw prior to Vengeance, Carlito made his debut on the Monday night roster and ended Shelton Benjamin’s eight-month reign with the Intercontinental Title thanks to some underhanded tactics. Days later, Benjamin would get a rematch to open the pay-per-view, and the result would be a solid bout between the athletic babyface Benjamin and the corner-cutting heel Carlito. But Carlito would once again resort to heel tactics to win, using an exposed turnbuckle to turn Benjamin’s offense against him.
5 Carlito vs. Chris Masters vs. Jeff Hardy vs. Johnny Nitro vs. Randy Orton vs. Super Crazy (Raw, 9/18/2006)
Carlito only ever had one reign with the Intercontinental Championship, but he had a few shots at it, including this forgotten Six-Pack Challenge on Raw for Johnny Nitro’s title. Featuring underrated midcard guys like Super Crazy and Chris Masters, this 15-minute bout is a forgotten gem of a TV match. It’s got a lot of really fun chaos and a fast pace but also gave everyone a chance to shine before Johnny Nitro regained against all odds.
4 Carlito vs. Chris Masters vs. John Cena vs. Kane vs. Kurt Angle vs. Shawn Michaels (New Year’s Revolution, 1/8/2006)
The original Elimination Chamber matches were for the World Heavyweight Title, but this fourth effort marked the first time the WWE Championship was on the line. While the outcome was Cena retaining the title only to fall to a surprise MITB cash-in from Edge, what happened in the Chamber shone a spotlight on some unexpected performers.
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The big story of this match was Chris Masters and Carlito teaming up to eliminate the other competitors -- that is, until it came down to John Cena. Carlito would take advantage and eliminate Masters, only to get quickly finished off by Cena. It was a fun surprise that made fans believe in both Carlito and Chris Masters.
3 Carlito vs. Chris Masters (Backlash, 4/30/2006)
Following their Elimination Chamber effort -- and despite Carlito’s treachery -- Carlito and Chris Masters formed a short-lived tag team, only to implode following their loss at WrestleMania 22.
In the aftermath, Carlito turned face and the two had a match to open up Backlash. While some fans were critical of Masters’ performance in this match, Carlito was the star here, with the live crowd being extremely invested in his success.
2 Carlito vs. Jeff Hardy (Raw 12/10/2007)
In another attempt at the IC strap, Carlito took on champion Jeff Hardy in a ladder match on the 15th-anniversary episode of Raw. Given the presence of Hardy, fans weren’t disappointed by the number of crazy ladder spots -- especially for a TV match -- but Carlito’s performance here was stellar as the story surrounded Carlito working Hardy’s leg. Given that every other match on the show was short, this 13-minute gem was even more of a standout bout.
1 Carlito vs. Ric Flair (Raw, 9/19/2005)
One night after losing the Intercontinental strap to Flair at Unforgiven -- the end of a three-month reign as champ -- Carlito got a rematch on Raw that blew the pay-per-view match out of the water. Running 20-minutes, the two delivered a surprising banger full of intensity thanks to Flair sustaining a legit eye injury over the course of the match. Flair retained, showing he’s still got a lot left in the tank, but Carlito ended up showing he could go for much longer than he usually got on television. That alone makes it Carlito’s best match ever.
