The Top 10 Mythical Sports Matchups We'd Love to See

October 20, 2009

What would happen if Michael Jordan faced off against Kobe Bryant? Is Roger Federer really better than Pete Sampras? Was Mario Lemieux more talented than Wayne Gretzky? If given the chance, could Mike Tyson win a first grade spelling bee?

These are the questions that society needs to spend more time focusing on. Nobody cares if God exists or who’s going to fix the economy. Only sexually inactive nerds with full-time jobs and honest tax returns ponder these issues. The real winners in this world spend their time debating fictional sports matchups while wearing football jerseys, that the wives they settled for have tried to throw away repeatedly. Thus, in an effort to reach out to you – “Guy who wrote his grad school thesis on why the 1985 Chicago Bears defense was the greatest of all time,” we have decided to put together a list of the 10 mythical sports matchups of the modern era we'd like to see. Nothing before the 1970s, though (because for as great as the 1961 racially segregated Crimson Tide were they’d lose by 21 points to any team in the SEC today).

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10. Roger Federer vs. Pete Sampras


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Not sure what it says about the game of tennis that the two most accomplished athletes in the history of the sport have the commercial appeal of a WNBA sex tape, but the amount of sheer talent and athleticism each of them demonstrated in their own eras is impossible to ignore. They have a combined 29 major championships, 125 tournament titles, two insanely hot wives, and a legacy of dominance usually reserved for teenagers who lie about their age in order to play in the Little League World Series.

The Argument: Jimmy Connors once said that “In an era of specialists — you're either a clay court specialist, a grass court specialist or a hard court specialist... or you're Roger Federer.” Sampras, on the other hand, had a tremendous serve (even Andre Agassi, the greatest returner of all-time, struggled with it) and was methodical in the way he would draw opponents into his serve and volley style.

Result: Assuming that both men are in their prime, Sampras wins a best of five match thanks to his powering serve and remarkable net play. He was a more strategic player and would have drawn Federer away from the baseline, where he is typically more comfortable.

9. 2001 Miami Hurricanes vs. 2009 Cleveland Browns


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The 2001 Miami Hurricanes are simply the greatest college football team ever assembled – by a long shot. NFL standouts Andre Johnson, Clinton Portis, Frank Gore, Jeremy Shockey, Kellen Winslow II, Bryant McKinnie, Vince Wilfork, William Joseph, D.J. Williams, Ed Reed, Mike Rumph, and Phillip Buchanon all contributed to a championship squad whose average margin of victory over the season was 32 points. Conversely, behind the incompetent arm of Derek Andrerson (who insults unemployed Americans every week by demonstrating that no matter how bad he is at his job, he won’t get fired), the Browns have shown a level of offensive futility that has forced upper management to start a Tim Couch re-signing rumor just to get the fans excited again.

The Argument: Most people will see a matchup between an NFL roster and a college team and automatically dismiss the idea of the Hurricanes winning. But consider this; in their rookie seasons (just months after they stopped paying foreign kids to take their "Golf Course Management" exams) Portis rushed for 1,500 yards, Shockey had 74 receptions, McKinnie and Wilfork became near-instant NFL starters and Reed was just two seasons away from being named the NFL Defensive Player of the Year.  This team was operating at an NFL level by the time they humiliated the Nebraska Cornhuskers in the BCS Championship Game.

Result: The Browns have the better all-around roster than their collegiate opponents, but the Hurricanes have more playmakers on their team. It would be difficult for Dorsey to adjust to the speed of an NFL defense, but with McKinnie protecting his blind side and Portis running the ball, the Canes would eventually find the Browns’ main weakness (football) and win the game. Miami 27- Cleveland 17.

8. 1989 San Francisco 49ers vs. 2004 New England Patriots


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This game is nothing more than an opportunity to finally have the sporting world stop comparing Tom Brady to Joe Montana every time he notches a come-from-behind victory over the Buffalo Bills. By pitting the 2004 Patriots (14-2 in the regular season and eventual Super Bowl champs) against Montana’s best team (also 14-2 with a Super Bowl championship), the world would finally see that Brady couldn’t hold a candle to the greatest quarterback of all time.

The argument: Joined by the greatest receiver of all time (Jerry Rice), Roger Craig, John Taylor, and a talented defense featuring Ronnie Lott and Charles Haley, the 49ers cruised to a 55-10 Super Bowl win, shutting down John Elway and the Denver Broncos. The New England Patriots, without any real talent at the wide receiver spot, scraped by the Philadelphia Eagles 24-21 in their championship victory.

The result:
Joe Montana picks apart a slightly overrated Patriots defense and finally ends the “Brady is the new Montana” talk spewing out of New England.

7. The WNBA vs. Total Bankruptcy


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This is a rivalry that’s been escalating for nearly a decade thanks to non-existent television ratings, questionably androgynous players, and a league that seems to have eliminated everything that’s actually exciting about the sport. The main problem here is that WNBA officials overestimated how many people sit around saying “You know, I really love basketball, but I wish there was a league where I could watch substantially less athletic women that I’m in no way attracted to play at a level comparable to my son’s junior high school team.”

The Argument:
With salaries getting out of control  (some players are signing massive five figure contracts) and the Ripley’s Museum cutting into the league’s freak show dollars, it seems like total bankruptcy may eliminate the league that David Stern once called “something I don’t think will immediately fail.”

Result: The WNBA shattered the 17-month point spread originally placed on this battle, but it looks like their luck is about to run out. On the plus side, if anybody is looking to hire a 6' 4 " day laborer with slightly feminine features and no ability to dunk a basketball, the WNBA unemployment center may be able to help.

6. 1992 Duke Blue Devils vs. 1982 North Carolina Tar Heels


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With all due respect to the 1996 Kentucky Wildcats and 1990 UNLV Runnin’ Rebels, the lure of setting up a game between the two greatest teams from this Tobacco road rivalry was too great to pass up. The 1992 Blue Devils won their second straight championship thanks to a collection of the most talented, albeit annoying, players to ever play under Mike Krzyzewski. College stars like Bobby Hurley, Christian Laettner, Grant Hill, and Cherokee Parks helped lead Duke to a 34-2 record and a championship ass-kicking over the “Fab Five” of Michigan. Exactly one decade earlier, North Carolina, led by a young Michael Jordan, James Worthy, and silky smooth Sam Perkins (who back then still looked like he was one puff away from spreading peanut butter on some Cheetos), the Tar Heels won a national title over the vaunted Georgetown Hoyas and their star center Patrick Ewing.

The argument: Forgetting the fact that Laettner essentially started the run of Duke NBA draft busts and is still the answer to the trivia question “Name that awkward white guy in the back of the 1992 Dream Team photo,” he was the most impressive college basketball player to hit the scene since Bill Walton sported a red afro in Westwood in the early 1970s. Laettner, Hurley, and Hill were an unstoppable trio that could have defeated anyone, from any generation… Except for maybe the greatest player to ever play the game. During the 1982 season Jordan was in his prime as a sophomore at North Carolina and had begun showing flashes of brilliance throughout the season.

The result: The Laettner-led Duke teams were some of the best we’ve ever seen, but the Tar Heels were simply a better squad. Worthy could have gone toe-to-toe with Laettner, and Jordan’s competitive edge was enough to defeat the Blue Devils.

5. Mike Tyson vs. an Elementary School Spelling Bee


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The Champ loves to use a lot of big words during his delightful post fight interviews, but have you ever wondered whether he’s able to actually spell them? “My style is impetuous. My defense is impregnable, and I'm just ferocious. I want your heart. I want to eat his children,” may sound like the thesis statement of a Rhodes Scholar, but it doesn’t mean that the baddest man on the planet to ever appear in a Bradley Cooper movie is able to correctly scribe his adorable sentiments about murdering children.

The Argument: Let’s be honest, the American public school system isn’t exactly a gateway to Ivy League Universities. Child literacy rates in this country pale in comparison to nations with militaries and consumer spending far below ours. Factoring in that Tyson didn’t get to use spell check while writing apologies to his victims from prison, and all of a sudden this becomes a closer fight than people expect.

Result: Tyson may be able to beat the majority of the first grade kids in a New York public school system spelling bee, but there’s always that one nerdy child in every classroom that uses the time he's stuffed in a locker to memorize the dictionary. Thus, it is unlikely that Tyson wins. Though, his post-bee press conference would probably be a lot of fun.

4. Tiger Woods vs. Jack Nicklaus


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Let’s pretend for a second that golf is a real sport (sorry fat kid that started playing because you couldn’t make the football team), and imagine the excitement that would surround a Tiger vs. Jack one round, winner take all playoff match. Woods is currently the richest athlete on the planet, has an incredibly hot Swedish wife, and has dominated some of the greatest athletes with 18 percent body fat in the entire world. No offense Mickelson, but maybe it’s time to say “no” to a cheeseburger or at least pick up a sports bra. But before Eldrick Tont Woods, or as his servants call him “Tiger,” was rising up the Forbes 500 list, a man by the name of Jack Nicklaus was reinventing the sport thanks to his precision putting and competitive nature.

The Argument: The classic childrens debate of who would win between a Tiger and a Bear comes to life in an event that Jim Nance has to change his sheets in the morning after dreaming about. Tiger is a near flawless player who can hit the long ball, make clutch putts, and procreate with an incredibly hot Scandinavian woman whenever he pleases (literally, can not stress that enough.) Nicklaus, on the other hand, was one of the most methodical players to ever pick up a club. He played the “sport” like a game of chess, planning several moves ahead.

Result: Let’s be honest. It’d be great to see these two legends battle it out in their prime, but there’s no way in hell Tiger loses this one. He’s just that much better.

3. 1984 Edmonton Oilers vs. 1992 Pittsburgh Penguins


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Every Canadian with a drinking problem and backyard hockey rink has often stayed up at night wondering if Mario Lemieux could have been a better player than Wayne Gretzky if he had stayed healthy over his entire career. Both were talented forwards with the ability to score at will during the same era, yet never played one another's best teams. For Gretzky, his early 1980s Oilers were considered to be one of the best of all time. Along with Mark Messier, Jari Kurri, Kevin Lowe, Paul Coffey, Grant Fuhr (and Peter Pocklington stealing all of their money), Gretzky won four Stanley Cups and the love of a city he would later leave for more money in Los Angeles. On the other side, Lemieux’s Penguins teams from the early 1990s were amongst the most explosive the sport had ever seen. A young Jaromir Jagr sporting the single greatest mullet in the history of sports, Ron Francis, Joe Mullin, Kevin Stevens, Rick Tocchet, Larry Murphy and not one, but two Samuelssons on the blue line helped Mario grab his second straight Stanley Cup in 1992.

The Argument:
Gretzky’s Oilers were better over a longer period of time, but Lemieux’s Penguins had a higher ceiling of talent at their peak. Neither goaltender was spectacular (Grant Fuhr never broke a .900 save percentage during any Stanley Cup season), so the result would likely be an extremely high scoring game filled with enough captivating highlights to let ESPN finally show a second hockey highlight during any of their bi-hourly Sportscenter broadcasts.

Result: As sacrilegious as this may sound to the Canadian hockey community, the Penguins win a seven game series over the Oilers. Lemieux and Jagr formed one of the greatest duos in hockey history, and their Hall of Fame role players put them over the top. There is simply too much talent on this Penguins’ roster for the Oilers offensive minded defensemen to handle.

2. 1998 New York Yankees vs. 1975 Cincinnati Reds


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Long before the New York Yankees began giving guys like Carl Pavano and Jason Giambi enough money to hire Alex Rodriguez to make balloon animals at Kate Hudson’s “Sorry Your Career is in the Toilet” birthday party, the Yankees built a dynasty with homegrown players and a reasonably-sized payroll. In 1998, Jorge Posada, Chuck Knoblach, Paul O’Neil, David Wells, Mariano Rivera, and a young Derek Jeter nailing his way through any brunette with a Maxim photo spread led the Bronx Bombers to a 114-win season and a World Series title. The only thing that could have stopped this roster would have been a Reds team led by Johnny Bench, Pete Rose, Joe Morgan, and Ken Griffey Sr. “The Big Red Machine” was an offensive force that crushed opponents and left little room for doubt in every one of their convincing victories.

The Argument:
The two most talented teams of the modern era both had great hitting and solid pitching. Neither had a glaring weakness and both had winning instincts littered throughout the dugout. This is just a matter of who gets hot at the right time.

The Result: The Yankees pitching staff, led by an unhittable Rivera, give the boys in pinstripes the slight edge in what would be one of the single greatest seven game series to ever be played.

1. 2001 Los Angeles Lakers vs. 1996 Chicago Bulls


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Assuming Kobe Bryant and Michael Jordan could fit both of their egos into whatever building every celebrity pretending to care about this matchup would pay obscene amounts of money to see, this would be the most incredible display of competitiveness in the history of any sport (and a wet dream for Nike’s advertising department). Hell, this thing writes itself: Catch a selfish prick whose gambling debts and disregard for social causes led to the most embarrassing Hall of Fame speech in recent memory take on an accused rapist who ratted out his teammate for adultery during a police investigation. The NBA, it’s faaannnntastic-ally filled with douchebags. The 1996 Bulls remain the most statistically accomplished team of all-time after collecting 72 regular season wins en route to their fourth of six NBA titles. Jordan, Scottie Pippen, a still-sane Dennis Rodman, Steve Kerr, Toni Kukoc, and apparently John Salley all helped the Bulls defeat the Seattle Supersonics in front of all 18 of Shawn Kemp’s illegitimate children. On the Lakers side of the ball, Bryant had a dominant Shaquille O’Neal, Derek Fisher, Robert Horry, and Rick Fox shouldering the load for a team that lost just one game throughout the entire postseason.

The Argument:
Kobe Bryant and Shaquille O’Neal formed one of the greatest tandems in NBA history. An unstoppable force of nature with an inside-outside presence that offered opposing defenses a problematic “pick your poison” dilemma all season. However, Michael Jordan simply doesn’t lose. He may be a lot of things, but a loser is definitely not one of them.

As painful as it is for somebody who has to watch skeezy foreigners crammed into sleeveless Lakers’ T-shirts four sizes too small every year in Los Angeles when the playoffs roll around, I just don’t see how the Bulls can come out on top here. Jordan may get the slight edge on Kobe, but how does Phil Jackson (the younger, less experienced one) stop Shaq from making Bill Wennington look like a helpless child underneath the basket? In the land of Hall of Fame wing players, the dominant center is king.