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The Summer Mega-Mailbag, Part II

Make no claims to the contrary — these are actual letters from actual readers.

If you missed Part I of the Summer Mega-Mailbag, click here. Here’s Part II.

Q: I enjoy your idea that certain players have earlier versions of themselves, such as Michael Jordan being the “Evolutionary David Thompson.” So is Lady Gaga the Evolutionary Britney Spears? And who is Evolutionary Kevin Federline?
— Nathan, New York

SG: Lady Gaga is the Evolutionary Madonna, not the Evolutionary Spears. Taylor Swift is the Evolutionary Spears; I know she’s fine now, but wait until she flips out and shaves her head in two years. And the Evolutionary Federline is unquestionably Levi Johnston. Who will probably end up dating Taylor Swift before everything’s said and done. Some other Evolutionaries just for the hell of it: Dana White (Vince McMahon); Angelina Jolie (Elizabeth Taylor); Chris Martin (Noel Gallagher); Ryan Seacrest (Dick Clark); Daniel Tosh (Joel McHale); Clay Bennett (Art Modell); David Kahn (former FEMA head Mike Brown).

Q: Lost in the bad financial advice given by sportswriters is the fact that working in Florida helps LeBron make more money due to taxes. Mark my words, soon a state will figure this out and instead of spending taxpayer dollars to fund stadiums, it will write a tax break into its tax code specifically for professional athletes. This state will then become the mecca for free agents and their sports teams will succeed.
— Gordon, Omaha, Neb.

SG: Note to Ohio legislators: Make it happen. Fifty-six years and counting. You need to stack the odds in your favor.

Q: My No. 1 reason for watching the World Cup: If you lose, something bad may happen to you. The Fear Factor is great. Some dictator, ruler or cartel will sell your family, house and car before your plane lands. Do you really think the North Korea goalie is still alive after giving up seven goals? Kim Jong Il has that guy floating in a dinghy somewhere.
— Mike Allen, Chicago

SG: All good points. It’s the only life-or-death event we have. I mean, even when Steve Bartman helped screw up the 2003 NLCS for Cubs fans, they didn’t kill him; they only made him move to Europe, change his name and start a new life as if he had joined the witness protection program. That’s totally different.

Q: If you could have one LeBron-related question answered, and only one, what would it be?
— Kenny, Chicago

SG: What happened in the Boston series between Game 3 and Game 6? My Dad was so crushed after Game 3 that he sold his tickets online for Game 4. We thought that series was over. LeBron was at the peak of his powers. So what turned a two-time MVP and one of the league’s most competitive guys into someone who seemed genuinely uninterested in Game 5 and couldn’t wait to get off the court in the last 90 seconds of Game 6? What happened? WHAT HAPPENED? How that wasn’t asked during “The Decision,” I will never know.

(My runner-up choice: Your Cavs teams were extraordinarily close in 2009 and 2010; what happened in the playoffs that made you guys fall apart and snowballed to the point that you didn’t even mention them during your one-hour “Decision” special? It was as if they were 11 waiters and bartenders with whom you worked at a restaurant for three weeks. You guys made such a big deal about being friends on and off the court; within five weeks, you were talking about how nice it would be to play with your good friends Wade and Bosh in Miami. What happened????????)

Q: I’m going to see “Sex and the City 2” tomorrow, by myself, no girlfriend, just so I can hate something more than the Lakers.
— Tommy, Reno, Nev.

SG: Received that e-mail one day after Game 7. And you thought that was the least redeemable movie ever made. Nope.

Q: Is the Gibson/Eckersley face-off the single greatest mustache confrontation in the history of sports?
— Alec, Kansas City, Mo.

SG: Only one man could answer this question: A longtime mustache aficionado and the head curator at the Useless Sports History Museum, ESPN’s own Chris Connelly. Here’s what Chris wrote me …

“Honestly? It doesn’t even seem like that would be the best baseball matchup: Sparky Lyle? Al Hrabosky? Mike Marshall? And 1988 — that’s gotta make you suspicious, right? That was late in the mustache era. The ’70s — whoo! Had to come from then. But Gossage retired … hairless Yaz. Rollie Fingers struck out … hairless Johnny Bench. So no such luck. My next thought: Clark Gillies versus Dave Schultz! But the YouTube footage is unclear. Though both had mustaches, it looks like Schultz has a beard and Gillies is clean-shaven for their bouts. My final answer? Joe Namath versus Ben Davidson (Fu Manchu plus Serious Handlebar, plus Ben gets bonus points for appearing in ‘Behind the Green Door’) in the Heidi Game.”

(Honorable mention from Simmons: Kareem Abdul-Jabbar punching out Kent Benson or, as it would come to be known, the most violent confrontation in mustache history. By the way, why isn’t there a book called “Mustache History”? Or at least a band?)

Q: Heard these rumors that the Yankees are going to buy Tottenham? Does this add a new dimension to the viable reasons for leaving a fan base? I mean you’ve only been a Spurs fan for, what, 12 months?
— Joe Sheehan, Spokane, Wash.

SG: Yup. And needless to say, there wouldn’t be a 13th month. I’d just switch to whatever team Landon Donovan was playing for. Which reminds me …

Q: The MLS is taking the stance that Donovan is not for sale. While I think it’s great to have Donovan in the MLS, this is not beneficial for American soccer. Donovan is in his prime, unlike Thierry Henry (on the downside of his career). Donovan should be playing in the EPL against the world’s best competition, not in the MLS (minor league soccer).
— Art Morath, Akron, Ohio

SG: Couldn’t agree more. I don’t see the MLS ever being bigger than Triple-A baseball in America, which is fine; Triple-A baseball sells out stadiums, works as a feeder system for the majors and remains lucrative. The hook for soccer is the national team, and by proxy, the success of the best American players. And, as Art points out, our players can only get better by playing against the best competition. So if we want to expose fledgling fans to the best possible soccer AND tap into the American/underdog/our-guys dynamic, the following scenario needs to happen: Donovan (the most famous American soccer player ever and still in his prime) needs to play overseas for a Premier League team (let’s say Everton, given that it already has Tim Howard); Everton needs to sign two other blue-chip Americans (let’s say Jozy Altidore and Michael Bradley) and turn itself into America’s Overseas Premier League Team; then, ESPN needs to sign a deal to show every game live for this team — and create a “Hard Knocks”-type show about a season in the life of this team.

Q: I think it should be your job (and every other non-Miami NBA fan, media member, etc.) to cause as much dissension on the Heat as possible. As such, I suggest always referring to the team as:

(A) Dwyane Wade’s Miami Heat;
(B) Dwyane Wade’s South Beach Heat;
(C) Dwyane Wade and company; and/or
(D) NBA champion Dwayne Wade and his Miami Heat.

Just sowing the seeds,
— Mike in Boston

SG: I love it! Let’s give it a whirl.

Q: You’re wrong about Chris Bosh not playing in big games. I direct you to the tapes of the 2003 NIT in his only year at Georgia Tech. He came to play!
— Chad, Los Angeles

SG: Bosh and Mike Miller combined: 31 NBA playoff games (all in the first round). Bosh hasn’t made the playoffs since 2008; Miller hasn’t made it since 2006. The good news: While playing for Dwyane Wade’s Miami Heat, they’ll be mentored by Juwan Howard (29 career playoff games in 16 seasons). Yes, these are the tiny straws that I’m holding onto these days as I slowly come to grips with Dwyane Wade’s Miami Heat winning 68 games as LeBron slaps up a 24-10-12.

(Two interesting notes off the last point: First, the 2011 MVP title is Kevin Durant’s to lose … unless LeBron tosses up the aforementioned triple-double for Dwyane Wade’s Miami Heat. Or something close. Which is entirely possible because it sure looks as if they’re going to position him as a 285-pound Magic 2.0 next season. And second, only Tiny Archibald and Wilt Chamberlain have “scoring season leader” and “assists season leader” on their résumé. Two crazy benchmarks sitting there waiting to be taken: the triple-double thing and the points/assists thing. That’s the best way for him to get us to forget about “The Decision” — win games and break records.)

Q: I just read on TMZ that Jennifer Capriati dated male adult film star Dale DaBone 2003-2009. How is that you have never mentioned this couple in any of your mailbags or analogies over the years. I am pretty sure you mentioned DaBone on a couple of occasions. Plus, is this the first case of a female celebrity/athelete dating a male adult star? Your readers need these answers.
— JJY the 3rd, Poconos of PA

SG: I didn’t mention it only because I never knew until recently. On a scale of 1 to 100, how disappointing was it that they didn’t get married and she didn’t start playing professionally with the name Jennifer DaBone? I have it at 96 right now. You could talk me into going higher.

Q: You have to install Ghana’s 2010 World Cup loss as the Perfect 10 of the Levels of Losing. Think about it: last minute of overtime, you’re about to go where no African team has gone before, and the ball IS going in before that Uruguayan slaps it away — then you shank the PK. Not just a city, not even a country, a whole CONTINENT’s dreams go down in raging flames of bitterness. You can’t get worse than that.
— Nate L., Los Angeles

SG: It’s only July, and we’ve somehow created four new levels of losing in 2010. You can see the revised list in the sidebar to the right (plus the last version of the column, from 2008). Here are the latest additions:

An offshoot of the Princeton Principle: When your team misses a chance to pull off a “Hoosiers”-like upset and make history by a fraction of an inch. You can’t be angry at the players because they did everything they could, but you can’t shake how close they came to immortality. Yeah, I’m talking to you, Butler fans. One more inch and you win the title on the single greatest basketball shot ever. You claim you aren’t bitter, but I guarantee you had a few too many drinks at least once in the past four months and that bitterness seeped out and you engaged someone in a “Really, that f—ing shot couldn’t have banked in? Really?” conversation. You did. Don’t lie.


When you blow a deciding game even though the other team is putting it on a silver platter and practically begging you to finish it off. You know, like blowing a double-digit lead in the second half of a Game 7 even though the other team shot 32 percent and its best player went 6-for-24 and had his fans greeting every brick with the same horrified silence Sarah Palin had when Bristol told her, “Guess what? Levi and I are engaged!”

See: LeBron, Cleveland, “The Decision.” The most devastating sports defeat that didn’t happen in a game.

Ghana blowing the potential winning penalty kick against Uruguay in the World Cup, then losing the game on penalty kicks a few minutes later. That was like all three Cleveland teams losing their worst possible game at the same time, only if Cleveland were a Third World country.

Q: Overheard in Heat front office, Miami, on Dec. 02, 2010: “Send Spoelstra off to do this, send Spoelstra off to do that! Let Spoelstra take care of some Mickey Mouse nightclub somewhere! Send Spoelstra to pick somebody up at the airport!”
— Matt, Seattle

SG: “That’s the way Wade and LeBron wanted it.”

“That’s not the way I wanted it! That’s not the way I wanted it! I was the incumbent coach, and I was passed over!”

Q: “It’s a Shame About Ray” is now about Ray Allen’s meltdown in the NBA Finals. You won’t undo this.
— Conrad, Los Angeles

SG: I have no counter until a Celtics-friendly band writes and records a song called “6-for-24,” then sends me the link to the video. Which, by the way, would earn all my column and Twitter traffic, as well as the traffic from pretty much every Boston blog or column. Just a hint. Speaking of the Celtics…

Q: In a few of your July 21 tweets you tweeted how the Celts could trade Rondo and a few other pieces for CP3 and possibly Emeka Okafor. My question is: Are you on drugs? The reason New Orleans would jump on that is because they know (and so does everyone else who has sense) that Paul is the fourth-best point guard in the league, behind Deron Williams (No. 3), Rondo (No. 2), and LeBron (No. 1), assuming of course that LBJ does in fact slide into the Magic Johnson-esque point-forward role.
— Steven, Jupiter, Fla.

SG: Apparently I was on drugs: In a rare error for the Picasso of the Trade Machine (I blame a bad batch of coffee), I forgot that Rondo was a base-year compensation guy thanks to last season’s extension, making it impossible capwise for Boston to deal him without getting a third team involved. And we all know menage-a-trades never work in the NBA. I do think Boston would have considered it because of what happened in the 2010 Finals (when Kobe played eight feet off Rondo in Game 7 and grabbed 15 rebounds because of it), because of Paul’s brilliance in 2008 and 2009 (when he slapped together the best back-to-back statistical seasons by any point guard since Oscar Robertson), and because Paul would solve their crunch-time woes. We’ll never know, though.

One more note: New Orleans can’t trade Paul unless it dumps Okafor’s contract (four years and $52 million remaining) and maybe even every other bad contract it has (one year of Peja Stojakovic for $14.3 million; two years of James Posey for $13 million). That rules out every suitor except Oklahoma City (this trade plus two No. 1 picks, which hinges on Paul agreeing to play for another small-market team); Orlando (which couldn’t give New Orleans a blue-chipper but could take back every bad contract with this trade); Portland (this trade plus picks, money and Greg Oden’s cell phone); Houston (this trade plus New York’s pick in 2011 or 2012 and $3 million, with the caveat that New Orleans buys out Yao and he re-signs with Houston); Dallas (two deals: Tyson Chandler for Okafor and $3 million, then this deal with Dallas throwing in another $3 million); and New York (this trade plus $3 million).

So if they’re really trading him — and by the way, he wanted out five weeks ago — we’re about to find out what’s important to Mr. Paul. If he wants to win titles, he pushes for Oklahoma City or Orlando. If he wants to be famous in a big market, play D’Antoni Ball and throw alley-oops to Amare Stoudemire as MSG goes bonkers, he pushes for New York. Either way, I think he’s gone.

(Note: That sudden silence you hear is 5 million Knicks fans being unable to breathe.)

Q: Dear Mr. Simmons,

Are you paid by the word? Your writing style reminds of high school and college writers who become too easily convinced “they can write!”

Perhaps you could consider dialing it down a notch?

Excess can be enthralling if you are Thomas Wolf[e], Dostoyevski or Herman Melville.

You are not.

You are a hyperactive, possibly neurotic sports hack writing about illiterate high-school-drop-out millionaires.

Who has the time to read your self-congratulatory rantings?

If you want to read GREAT sportswriting look to “The Guardian.”

It’s not about YOU. Try writing about the actual event. Once. Briefly.

It’s called journalism.
— Craig Pedersen, New York

SG: Put it this way: I could have gone on a writer’s retreat with 10 buddies, spent four solid days trying to come up with the douchiest e-mail possible and still not done better than Craig Pedersen of New York.

Q: Has there ever been a worse sports contract than Elin Woods for 6yrs/$100m?
— Daveg34 (via Twitter)

SG: Come on, in the summer when Joe Johnson got $120 million, David Lee and Rudy Gay got $80 million, Brendan Haywood got $55 million, and Drew Gooden/Darko Milicic/Amir Johnson/Channing Frye got a combined $116 million, I think Elin for a rumored $100 million sounds more than fair. That’s a good price for a franchise Swedish trophy wife.

Q: When I heard about the Elin Woods divorce settlement, the first thing I thought about was that she now could buy a sports franchise. I think she owes it to the world to buy an NBA team and become the world’s first MILF owner.
— Harvey, Miami

SG: You just described the plot of HBO’s “First and Ten,” or, as every horny teenager from the mid-’80s remembers it, “That football show with a skinny and surprisingly hot Delta Burke, O.J. Simpson, Ogre from ‘Revenge of the Nerds,’ USFL footage and at least one gratuitous sex scene per show.” Uh-oh, I think I just gave Spike a bad idea for a remake.

Q: For the upcoming Miami season, what do you think would be the best chant to really get under LeBron’s skin? It should be something to call out his second-banana status on the Heat. Maybe something like Sidekick, or my personal favorite, Robin.
— Rick, Livingston, N.J.

SG: I vote for these three …

1. “You Sold Out! You Sold Out! You Sold Out!”

2. “De-lon-tay! De-lon-tay! Del-lon-tay!”

3. (Derisive singing) “Siiiiiiiiide-kick. Siiiiiiiiiiiiide-kick. Siiiiiiiiiiiide-kick.”

(Note: Of those three, the last one will hurt the most and possibly propel him into “I’ll show you who’s the sidekick!” mode.)

Q: If you look back on all the episodes of “Seinfeld” that dealt with Jerry and Co. frantically racing across town for whatever reason or missing somebody at a restaurant or bar by a couple of minutes, a BlackBerry or iPhone would’ve solved all their problems. Larry David and Jerry Seinfeld are lucky they made the show when they did (before cell phones went mainstream) because there’s no way “Seinfeld” works in 2010.
— Steve Clark, Fort Wayne, Ind.

SG: Thanks for ruining “Seinfeld” reruns for me; I can’t watch the show since I read this e-mail. Next up for Steve Clark: Figuring out ways to piss on Christmas and three-day weekends.

Q: How long until the Timberwolves trade for Greg Oden to complete the botched draft pick trio? Beasley, Milicic and Oden — unstoppable!
— Chad, Detroit Lakes, Minn.

SG: Minnesota fans everywhere are screaming, “No! He just gave David Kahn his next dumb idea! No! Why did you print that????”

Q: I’m sitting at my cubicle at work and reading about the potential Al Jefferson trade to Utah. Utah would supposedly give up … NOBODY! I know Al regressed a little last season, but this is one of the handful of guys who can score in the post and average 20 and 10, and Kahn is giving him away for the chance to draft more PGs and SFs?? The reasoning: There’s a logjam in the front court because of the Beasley trade and Darko re-signing. You know how you avoid that logjam: DON’T RE-SIGN DARKO OR TRADE FOR BEASLEY. How does this man have my dream job and make 10 times more than me while I’m stuck in this cubicle??? Answer me!
— Patrick, Los Angeles

SG: Kahn!!!!!!!!!!!!



Q: Who is the funniest man alive right now? Personally I like Zach Galifianiakis — he’s the Kevin Durant of this category. We know he will be great, but he isn’t quite there yet. I’m still taking him.
— Joey Miller, Dallas

SG: I spent way too much time thinking about this. The short answer: Yes. 2009 belonged to Galifianiakis over any other funny person. Not sure about 2010 yet.

The long answer: With the NBA, I can just click on a list of MVPs for the past 50 years that gives me a general idea of “Who was the best player alive for that year?” We don’t have this for the Funniest Person Alive title, and really, we should. You have to nail at least one of these questions to qualify for that given year: Were you in the hottest comedy of the year or, even better, in the middle of a run of hot comedies? Were you carrying SNL? Did you have an iconic stand-up special, cable TV show, late-night show or comedy series? Did you routinely crush any late-night appearance or SNL hosting gig? Did you have a huge approval rating with little to no backlash? Do we associate that year with you to some degree? I need resonance beyond just cult affection, which unfortunately rules out the great Bill Hicks (who has a strong case for 1990).

For instance: 1982, 1983, 1984 … Eddie Murphy. Period. That was the Eddie Era. SNL, “Delirious,” “48 Hrs.,” “Trading Places,” “Beverly Hills Cop.” Done. There was no doubt whatsoever. And sure, there might have been some doubt in other years. But here’s what I am thinking for guys in my lifetime (starting in 1975, when I could start remembering stuff, along with input from 10-12 friends).

1975: Richard Pryor
Best stand-up comedian alive (and the most respected). Also crushed his only SNL hosting gig ever with its first legitimately great show and water cooler sketch.

1976: Chevy Chase
SNL’s first breakout star as it became a national phenomenon. He also made the worst move in Funniest Guy history by leaving the show as he was wrapping up his Funniest Guy season. Even “The Decision” was a better idea.

1977-78: John Belushi
Replaced Chase as SNL’s meal ticket in ’77, then had the single best year in Funny Guy History a year later: starred on SNL (in its biggest year ever, when audiences climbed to more than 30 million per episode); starred in “Animal House” (the No. 1 comedy of 1978 and a first-ballot Hall of Famer); had the No. 1 album (the Blues Brothers’ first album). No. 1 in TV, movies and music at the same time? I’m almost positive this will never happen again. And also, if you put all the funniest people ever at the funniest points of their lives in one room, I think he’d be the alpha dog thanks to force of personality. So there’s that.

1979: Robin Williams, Steve Martin (tie)
“Mork and Mindy” plus a big stand-up career for Williams; “The Jerk” plus a best-selling comedy album plus “official best SNL host ever” status for Martin.

1980: Rodney Dangerfield
His breakout year with “Caddyshack,” killer stand-up, killer Carson appearances, a Grammy-winning comedy album, even a Rolling Stone cover. Our oldest winner.

1981: Bill Murray
Carried “Stripes” one year after “Caddyshack.” Tough year for comedy with cocaine was ruining nearly everybody at this point.

1982-84: Eddie Murphy
The best three-year run anyone has had. Like Bird’s three straight MVPs. And by the way, “Beverly Hills Cop” is still the No. 1 comedy of all time if you use adjusted gross numbers.

(Random note: Sam Kinison’s 1984 spot on Dangerfield’s “Young Comedians” special has to be commemorated in some way. At the time, it was the funniest six minutes that had ever happened, and it could have single-handedly won him the title in almost any other year. It’s also the hardest I have ever laughed without drugs being involved. Sadly, I can’t link to it because of the language and because it crosses about 35 lines of decency. But it’s easily found, if you catch my drift.)

1985-86: David Letterman
Went from “cult hero” to “established mainstream star,” ushered in the Ironic Comedy Era, pushed the comedy envelope as far as it could go, and if you want to dig deeper, supplanted Carson as the den father for that generation of up-and-comers and new superstars (Murphy, Leno, Seinfeld, Michael Keaton, Tom Hanks, Howard Stern, etc.) … and, on a personal note, had a bigger influence on me than anyone other than my parents. One of two people I could never meet because I would crumble like a crumb cake. (You can guess the other.)

1987: Jay Leno, Howard Stern (tie)
Seems like a million years ago, but Leno’s frequent appearances on Letterman’s show and enjoyable “Tonight Show” guest host spots stole the ’87 title from Letterman just because he seemed newer and fresher. (Note: The Leno-Letterman spot always delivered the goods. They were unbelievable together. That’s what made it so unbelievable when Leno backstabbed him for the “Tonight Show” job.) Meanwhile, Stern’s morning show had become a tri-state phenomenon and reached the point that people were trading cassette tapes; he even landed a Fox pilot that year.

1988: Eddie Murphy
Reclaimed the throne with “Coming to America” one year after “Raw.” Also, Arsenio Hall’s show had taken off and Eddie was a frequent guest. The last great Eddie year. Alas.

1989: Dana Carvey
SNL’s first breakout star in five years thanks to the Church Lady, his Bush Senior impersonation and a bunch of other things that didn’t really hold up. What’s weird is that Phil Hartman’s SNL stuff held up much better, only it took Carvey’s leaving for people to realize how great Hartman was.

1990: Billy Crystal
Never had a career year but accumulated enough momentum from his stupendous SNL stint (1984-85), “City Slickers,” his HBO comedy special and his late-night guest spots that his 1990 Oscars host job (the best ever to that point) wins him the award in a weak year. FYI: You could make a decent Hicks case here, but he just wasn’t well-known enough.

1991: Jerry Seinfeld
The year his show started taking off, much to the delight of everyone who loved him from his Letterman/Carson spots and the four episodes from the previous summer. I will never forget me and my buddy Kurt Sanger trying to persuade everyone else we knew in college to watch the first episode of Season 2 with us (January 1991) and only a couple of them biting.

1992: Jerry Seinfeld, Mike Myers (tie)
Seinfeld’s show became a smash hit; Myers was SNL’s biggest star during a resurgent era and also made a hit movie (“Wayne’s World,” now the most dated comedy of all time and totally weird to watch, although the “Bohemian Rhapsody” scene remains funny).

1993: Mike Myers
Weak year. Myers had SNL, “Wayne’s World 2” and “So I Married An Axe Murderer.” You could talk me into giving the entire “Simpsons” writing staff this spot just to get them on the list.

1994: Jim Carrey
“Ace Ventura,” “The Mask” and “Dumb & Dumber.” Has anyone ever gone 3-for-3 with smash hits in one year? Now he’s just a crazy person on Twitter.

1995: Chris Farley
His long-awaited “I always loved Chris Farley and now I feel totally vindicated because I knew he was going to be famous” year with “Tommy Boy.” Which still holds up, by the way. Silver medal to Norm MacDonald for crushing it on “Weekend Update” during and after the O.J. trial.

1996: Chris Rock
He underachieved on SNL to the point that, when he switched to “In Living Color” for one year, nobody gave a crap. By 1995, he had fallen into the “doing guest spots on ‘Martin’ and ‘Fresh Prince of Bel Air'” stage of his career. And then, out of nowhere … “Bring the Pain” happened. The best stand-up special since Eddie in his prime. Who knew?

1997: Garry Shandling
The best season ever (Season 5) of one of the greatest comedies ever (“The Larry Sanders Show”) peaks with “The Roast” (the single funniest episode in the history of the show). Good enough to win a weak year.

1998: Adam Sandler
Became an A-list comedy franchise with “The Wedding Singer” and “The Waterboy.” Weak year otherwise.

1999: Mike Myers, Chris Rock (tie)
“Austin Powers 2” (and A-list celeb status) for Myers; “Bigger and Blacker” special and an inventive weekly HBO show for Rock.

2000: Will Ferrell
At the height of his SNL powers at this point thanks to his Dubya impersonation. You could make a very strong “Will Ferrell was the greatest cast member in the history of SNL” case.

2001: Matt Stone and Trey Parker (tie)
A seminal season for “South Park” (Season 5) peaks with the ballsy Osama episode just eight weeks after 9/11. Weird year for comedy in general. You could make a strong case for Ricky Gervais here; I would give it to him except for the fact that I hate British people.

2002: Larry David
His best “Curb Your Enthusiasm” season (Season 3), and it featured my single favorite episode (the one with Krazee-Eyez Killa).

2003: Dave Chappelle
Season 1. Enough said. The last unequivocal, there-is-no-doubt-whatsoever-that-he-has-the-title comedy season.

2004: Dave Chappelle, Jon Stewart (tie)
Season 2 for Chappelle and a breakout year for Stewart (the 2004 election, his “Crossfire” appearance, the release of his book and his Peabody Award).

2005: Steve Carell
“The Office” takes off, and “The 40-Year-Old Virgin” hits theaters. Good enough to take a splintered year. Thanks to the Internet and cable booms, comedy became so specialized that it got infinitely more difficult to say one person was the Funniest Man Alive. My personal choice: Ferrell again, just because of “Anchorman.”

2006: Sacha Baron Cohen
Borat. More than enough.

2007: Larry David
Comeback year for “Curb” as the Blacks move into Larry’s house. Runner-up: Judd Apatow.

2008: Tina Fey
“30 Rock” takes off, and Palin falls into her lap. Our first and only woman!

2009: Zach Galifianiakis
His “Hangover” role was funnier than anything anyone else did … right?

2010: ????????
Five months to go. Haven’t had a breakout star yet. Unless you count the double rainbow guy. So there you go.

Q: I nominate Jor-El for worst parent of the century. It’s highly irresponsible to put a naked baby in a space ship made of sharp rocks. It’s a good thing there is no child services on Krypton or his ass would be locked up.
— Brendon P, Cedar Falls, Iowa

SG: Well, I guess it’s time.

Q: So I’m up late on Saturday night watching MTV’s “True Life.” It’s an episode in which it follows two people who aren’t happy about their gender. One guy is super excited about getting his boobs so he can start the process of becoming a woman. He gets his new boobs and when we finally get to see them, they are blurred. Wait a minute … isn’t he still a guy? What’s the difference between this and anyone on “The Biggest Loser”? Also, it follows a girl who is getting her boobs removed. They show her in the operation room and when her boobs are getting cut out, there is no blur to be seen. Six weeks later, they pull off the bandages and there they are. All stitched up for me to see. No blurs to be found. So now I’m really perplexed. When do the rules of what to/what not to blur set in?
— Mike Gath, Austin, Texas

SG: Approaching …

Q: If you could replace any character in movie history with yourself, who would it be and why? My vote is for you to replace Goose in “Top Gun.” You get to kiss a young and hot Meg Ryan, get a nickname no one will ever forget, plus you seem like the kind of guy that would love to play shirtless volleyball with Tom Cruise and Val Kilmer, and next to Cruise you would look 6-foot-9. I don’t think anyone would watch it but still.
–Scott Smith, Madison, Wis.

SG: Coming in for the landing …

Q: Am I the only one who does the following? Whenever I get more than about three-fourths of the way down your mailbag, I start scrolling very slowly through each question and answer so that the next one doesn’t appear. That way, I won’t errantly glance down and see the “Yup, these are my readers” line below, which ruins the surprise. It seems silly but also necessary — it’s much more satisfying to read the e-mail in anticipation of the eventual YTAMR.
— Ari Ofsevit, Boston

SG: Yup, these are my readers.

Bill Simmons is a columnist for and the author of the recent New York Times best-seller “The Book of Basketball.” For every Simmons column and podcast, check out Sports Guy’s World. Follow him on Twitter at