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10 Awesome Celebrity Boxing Matches That We Want to See

Donald Trump, Geico Gecko, Regis Philbin
Matthew Lewis, Getty Images / Geico / Cindy Ord, Getty Images

Lenny Dykstra’s battle with Jose Canseco in one of those dignified celebrity boxing matches never took place over the weekend after Dykstra pulled out for reasons that remain unclear. While no victor emerged, fans who bought tickets for the bout came out the loser because they missed what could’ve been the biggest slugfest since Dr. Pepper conquered all but 10 calories.

The fact that these two former major leaguers were slated to tussle got us thinking, though. What other celebrities would we like to see tie on the gloves and go for a few rounds? Here’s a look:

Charlie Sheen, Chuck Lorre
Christopher Polk / David Livingston, Getty Images

Charlie Sheen versus Chuck Lorre

This fight should take place on CBS in the time slot when ‘Two and a Half Men’ currently airs. Think about it. Ratings have slipped now that the novelty of Ashton Kutcher joining the cast has worn off, so putting Sheen and Lorre in the ring could only help CBS bring in viewers, while they rekindle the very ugly spat that led to Sheen’s very public exit from the onetime very hit series. Sheen has an athletic background, so we think he’d come out on the “winning” end of this one.

David Stern, Billy Hunter
Patrick McDermott, Getty Images

David Stern versus Billy Hunter

The NBA lockout shows no signs of coming to an end, so enough of the two sides negotiating. Throw the commissioner in the ring with Hunter, who heads up the players union. If Stern wins, the owners get everything they want. If Hunter wins, the players get everything they want. How simple is that?

Regis Philbin, Michael Gelman
Cindy Ord / Stephen Lovekin, Getty Images

Regis Philbin versus Gelman

Regis is leaving ‘Live!’ after 25 years later this month. He reportedly didn’t get the contract he wanted, so you know he’s got some pent-up rage, which we’d love to see unleashed on his longtime foil and producer, Gelman. They say you should come out swinging, but why not go out that way, Reege?

Herman Cain, Newt Gingrich, Ron Paul, Mitt Romney
Stephen Morton, Getty Images

Mitt Romney versus Herman Cain versus New Gingrich versus Ron Paul

Does anyone really know what any candidate is talking about in a presidential debate? They all pretty much say the same thing, using worn-out phrases like “healthcare reform,” “tax code” and “fiscal responsibility.” So, let’s scrap their mumbo jumbo, toss out the fancy suits and wingtip shoes and go round-robin in a series of matches. Whoever comes out with the best record scores the GOP nomination. Anybody willing to literally kick some butt is a guy we’d want leading our country.

Kris Humphries, Lindsay Lohan
Getty Images

Kris Humphries versus Michael Lohan

Humphries says Kim Kardashian’s decision to file for divorce caught him by surprise. He’s also not making any money because of the NBA lockout. Lohan recently landed in the clink, not once, but twice in the span of a few days, and daughter Lindsay did the same when she was sentenced to 30 days for violating her probation, although she did get out after a few hours. Clearly, these are two men with issues, so why not let them pound out their aggressions on each other?

Donald Trump, Earth
Matthew Lewis, Getty Images / NASA Goddard Photo and Video, Flickr

Donald Trump versus The World

The Donald is the original bully, picking fights with everyone from President Obama to Jon Stewart to Jerry Seinfeld. They say actions speak louder than words, so we propose Trump finally stops running his yapper and let his fists do the talking by jumping into the ring with all the people who’ve annoyed him over the years. The only problem is where can you find a boxing ring big enough to hold all those people — well, at least without Trump building one and then bragging about it?

Jay Leno, Conan O'Brien
Kevin Winter / Frazer Harrison, Getty Images

Jay Leno versus Conan O’Brien

Okay, the hullabaloo over who gets to host ‘The Tonight Show’ is long done, but you know Conan would like to get a piece of Leno. He had the most revered show on television taken from him and given right back to his predecessor while the entire watched the drama unfold. Conan has rebounded with his own late night show on TBS, but, c’mon, they gave George Lopez a show, so that’s not much of a consolation prize. His downward spiral from ‘The Tonight Show’ to cable is like drinking Cognac before someone swipes it from you in favor of Natty Light. Let Conan take a few swings at Jay’s jutting-down-like-a-map-of Florida chin. It’ll make him feel a whole lot better.

Johnny Depp, George Clooney
Stuart Wilson / Alberto E. Rodriguez, Getty Images

Johnny Depp versus George Clooney

Women love these guys and have loved them for several years. It’d be nice to see them knock each other around for no other reason than to mess up their dreamy mugs so they resemble the rest of us mere regular-looking mortals. Of course, they’re so darned handsome, women would probably swoon even more at their black eyes and split lips, which means our dream matchup here would turn into a nightmare.

Angelina Jolie, Jeninfer Aniston
Jason Merritt, Getty Images

Angelina Jolie versus Jennifer Aniston

Call this the catfight to end all catfights. The hype, not to mention the Pay-Per-View ratings, would go through the roof. These two can say all they want that they’ve moved on from their roles in the Brad Pitt love triangle, but, come on, we all know there’s bad blood. Angie basically poached Brad from Jen, who has maintained a brave face while carrying on a parade of fleeting relationships, so you know she’s gotta harbor some resentment. This would be her chance to show everyone just how much. And we’ve seen Jolie kick butt in movies — let’s see how she does in real life.

The General, Geiko Gecko
The General, Geiko

The General versus the Geico gecko

What is it about weird insurance spokesmen? The General is militant in a field where it’s not necessary and the gecko comes off more like a lover than a fighter, but they are both extremely and strangely passionate about saving people money on their car insurance, so let ‘em take their competitive fires between the ropes. And to make it more interesting, how about Flo from Progressive serve as the ring card girl?

Drew Weisholtz is a funny guy. Unless you didn’t like this, in which case he’s simply using a pseudonym. He’s written for ABC and other online outlets and does standup comedy in front of actual people. You can follow him on Twitter @undrstoodgenius.

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