I enjoy Halloween so much that I once wrote an entire fake SportsCentury show about Michael Myers, in 2002. No, really. It’s in the ESPN.com archives and everything.

I enjoy Halloween so much that, back in 2007, my wife went into labor with my son on Halloween afternoon … and I was briefly crestfallen when midnight struck and he hadn’t popped out yet.

I enjoy Halloween so much that I joked that same night, “If this kid is born on Halloween, we have to name him Michael Myers Simmons,” and my wife didn’t think I was kidding.

I enjoy Halloween so much that I wrote this last year: “Being a parent of young kids sucks. Don’t let anyone tell you differently. About six months ago, I wanted to start a Twitter account of quotes my wife screamed in the heat of those my-kids-are-driving-me-crazy-moments such as these: ‘If you don’t stop crying, I am going to stick you in the microwave!!!!’ and ‘Fine, climb up the stairs again; I hope you fall down, I really do!’ She wouldn’t let me because she thought child services would arrest us. The truth is, every parent snaps from time to time. We can’t help it. Our kids’ job is to suck all forms of life from us, frighten us, embarrass us in public and prevent us from sleeping until they turn four. We pretend it’s not so bad when, really, it’s mostly horrible and even somewhat indefensible. But — and this is a big but — they parcel out just enough, ‘Wow, I’m so glad I had kids’ moments to make it all worth it. And that’s what Halloween is: an entire ‘Wow, I’m so glad I had kids’ day. At least until they eat too much chocolate and wake us up at 5 a.m. the next morning because they’re Exorcist vomiting.”

I enjoy Halloween even though I hate getting dressed up for Halloween. In college, I went as Brandon Walsh two years in a row — I just wore a blue sports jacket, a white t-shirt and fake sideburns. The only time I ever showed any imagination was back in 1998, when Halloween H20 came out. I bought a black gas-station attendant outfit and wore that along with my Michael Myers mask to the theater. With my future wife in tow. Wait, I shouldn’t have admitted this.

I enjoy Halloween so much that I once wrote this: “Kids love Halloween because of the candy. Adults love Halloween because it’s the best party of the year, the best chance to see a co-worker or fellow student dressed like a hooker, the best day to spend with your kids and, if that’s not enough, the setting for the best horror movie of all time. And NFL fans love Halloween because it signifies the end of a glorified exhibition season. Come November, the real season begins.”

I enjoy Halloween so much that I kept figuring out ways to suggest Halloween costumes for readers in Mailbags and NFL columns over the past few Octobers. We thought it would be fun to look through them again, if only for some of the now-dated sports and pop culture references (except for the Donna Martin reference, which was dated when I wrote it).

2005

Q: Do you have any ideas for cool Halloween costumes? I’m sick of the slutty nurse, slutty french maid, slutty [insert female occupation here]. What is the Sports Gal going as?
–Jen M., Middletown, N.J.

SG: The Sports Gal is going as a mother of a young baby who doesn’t sleep enough — a permanent scowl and eye bags and you’re all set. But I’m glad you asked because a person’s Halloween costume says a lot about them (especially females). Halloween costume choices are distant cousins of playing pool at a bar. In bar pool, there are two types of women — the ones who bend over because that’s the only real way to make a successful shot, or the ones who perform a half-crouch so their butt doesn’t stick out … hence, jeopardizing their chances and proving to everyone that they don’t really care about winning the game, and they’re only playing so guys will check them out.

(Just for the record, I dated only two half-crouchers, and neither of them lasted long. Any woman worth her salt will bend over, stick her butt out, try to make the shot and deal with the consequences of random drunken dudes leering at her rear end. This separates the keepers from the pretenders if you’re choosing a mate for life — I’m telling you. Don’t end up with a half-croucher. These are also the women who wear makeup to bed during the first 6-7 weeks you’re dating and pretend they never go to the bathroom until you’ve been dating for like four years.)

Anyway, here are the three groups of female Halloween costumes:

Group A: Girls who use their costumes as an excuse to get attention from guys. Common examples include the slutty bunny/cat/genie/nurse/angel/cop/french maid/schoolgirl or slutty anything-with-a-tail. Please note, I’m not against any of these costumes — in fact, I support and applaud them. Mainly because they can be the equivalent of somebody holding up a sign and saying either, “I’m up for some casual sex tonight” or “I’m definitely ready to start cheating on my boyfriend.” But here’s the problem: Sometimes the girls who make these choices are the quiet/uptight/prudish types who think this is their way of letting loose for the year. So it’s almost like playing roulette, trying to figure out what their intentions are.

(By the way, for a less trendy, somewhat slutty costume, you might want to break out the cowgirl or dominatrix gimmicks — more elaborate, more expensive, but also more respectable, more commendable. You can’t go wrong. If you don’t have the money, steal it.)

Group B: Girls who go overboard and end up stuck wearing a sweaty mask or costume that legitimately hinders them for the entire night. This is bad — like Donna Martin dressing as a mermaid for the West Beverly High Halloween party. Could potentially kill your night. Plus, you always get like four monster zits after wearing a sweaty Halloween mask for too long.

Group C: Girls who are downright creative with their costumes. For instance, two years ago at the “Jimmy Kimmel Live” Halloween party, Sarah Silverman dressed up as Sexy Hitler (basically, Hitler in drag as a sexy woman). People at the party were floored. In fact, my editors are floored right now as they decide whether this paragraph can run. But those are the costumes you end up remembering, not the 550,000,000th person who dressed up like a slutty cat.

Without further ado, four suggestions for Halloween, 2005:

Costume No. 1: “Taradise”
This bangs out the “I’m still cute, you might want to think about hooking up with me later” angle, but it’s also funny — you need a blonde wig, a slutty outfit, a liquor bottle, smeared lipstick, fake scrapes on your knees and giant fake knockers. And you just need to stumble around and scream crazy things while your friends hold you up. Later, when you get drunk and start acting like this for real, people will assume that you’re still playing the “Taradise” role. This also works for Courtney Love if you want to go in that direction.

2011 Update: Who knew this would work best for Lindsay Lohan six years later???

Costume No. 2: Stripper
If you’re going slutty, go all out — wear a stripper’s outfit, stick dollar bills in your garter belt and carry around a makeshift stripper’s pole. Why not go all the way? People will notice you. Especially if you’re attending a party that includes Clinton Portis.

Costume No. 3: Nicole Richie
Dress in a skeleton outfit, only with fancy clothes on. Can’t miss and a guaranteed laugh when someone asks who you are.

2011 Update: LeAnn Rimes?

Costume No. 4: Generic Women’s College Basketball Coach
My personal favorite. First, go to Marshall’s and buy the ugliest beige pants suit you can find. Second, buy a Nancy Reagan wig. Third, buy 8-inch high heels and practice walking awkwardly in them. Fourth, learn how to do that whistle where you stick your index and pinky fingers in your mouth, then make an excruciatingly loud noise. And you’re good to go.

2006

Q: “Last year you had a list of suggestions for female Halloween costumes, including a Tara Reid costume which made me laugh out loud. Not sure if anyone pointed this out to you yet, but this year there is actually a store-made Tara Reid costume available, which means there will be tons of drunken frat boys dressed as Tara this Halloween. What good suggestions do you have for the ladies this year?”
–Kelly, Hoboken, NJ

SG: First of all, I’m delighted that there will be hundreds of Tara Reids running around on Halloween. This could be the event that causes Carson Daly to finally drop below the 170-pound mark and start looking like Christian Bale in “The Machinist.” My four costume ideas for this year:

No. 1: Lindsay Lohan
Wear a red wig and look completely strung out for about 30 minutes. Then go to the bathroom, fix your makeup, stick a pair of grapefruits in your bra and come back out looking like a million bucks. Thirty minutes later, go back in the bathroom, mess your makeup up and take the grapefruits out. And just keep rotating the two looks all night and confusing the hell out of every guy there.

2011 Update: If you cross the 2005 Taradise idea with the 2006 Lindsay idea, you might really have something.

No. 2: A female figure skater and her coach
You need a figure skating outfit, ice skates and a male friend willing to act as effeminate as possible for the entire night. Plus, this is one of those secretly slutty columns that will look better as the night goes on.

No. 3: Carrie covered in pig blood on her prom night
My personal favorite. Buy a hideous prom dress and a red wig, then dump a couple of quarts of cranberry juice all over yourself and walk around with a crazy look on your face like you’re Ron Artest after the Palace melee. There will be at least one guy at the party who gets turned on by crazy chicks and will want to hook up with you. You can’t lose.

No. 4: Suzy Kolber and Joe Namath
Just a perky outfit, a short wig and a microphone for the girl and a Jets jersey and fake nose for the guy and you’re ready to go. Not only can the guy playing Namath drink all night without hurting his impersonation, but other guys will step in asking, “I just want to kiss you, I just want to kiss you.” Any costume that leads to multiple guys asking to kiss you has to be a winner.

2007

Note: My wife wrote a sidebar for my NFL column during the 2007 season. Here’s what she wrote about Halloween that year. PS: I don’t think the “Deal or No Deal” idea would work anymore, but the one in the last paragraph would. As would the one from my friend, Geoff.

Me and two friends dressed up like “Deal or No Deal” models for a Halloween party last weekend. We bought silver suitcases and wore black dresses and wigs, although we didn’t go super-slutty or anything. Girls always used to use Halloween as an excuse to dress like total sluts. Now you don’t need an excuse because it’s OK to dress like a slut in any situation. If you plan on dressing like a cat or a nurse this weekend, or if you plan on wearing a push-up bra with a shirt unbuttoned to your navel, just head to a club after the party and nobody will realize you’re wearing a costume.

As for Bill, he was supposed to go as Howie Mandel, but his huge head couldn’t fit into the bald cap we bought. So he wore a cowboy hat and cowboy shirt and went as a country-western singer. Total cop-out costume! He didn’t even care that it didn’t look like he cared. The year we started dating, Bill took me to Halloween H20 dressed up like Michael Myers and completely embarrassed me and freaked out everyone else in the theater, but I kind of liked that about him. Now he won’t even spend five minutes thinking up a Halloween costume even though he knows I love Halloween. I don’t get him sometimes.

So we went to the party and half the people put thought into their costumes, while the other half put their costumes together in 90 seconds like Bill did. There were some good ones but nothing really stood out. That got me thinking about my favorite Halloween costume: A few years ago, my friend Allie was a one-night stand. She wore a black cocktail dress that was wrinkled and had some stains on it. She had a ripped stocking, broken heel, smudged lipstick and messed-up hair like she just rolled out of someone else’s bed. The whole night she paraded around with things falling out of her purse like she was in the middle of a walk of shame. It sounded like the funniest thing ever. This week I told Bill about Allie’s costume and made the mistake of asking what his favorite Halloween costume was. He said it was the time his friend Geoff dressed as a poop. I guarantee that my second husband will appreciate Halloween.

2011 Update: If you want to dress like a poop for Halloween, here’s what Geoff did — wore a brown sack, sprayed it with fart spray and stuck toilet paper all over it. Ladies and gentleman, the best man in my wedding, Geoff Gallo!

2009

Q: I’m a 24-year-old female looking for a Halloween costume that (a) isn’t skanky (does that exist anymore??) and (b) will piss off as many people in NYC as possible. I’m from MA and it goes without saying a huge NE sports fan and somehow got sucked into living and working in Times Square for the past two years so I’d love a costume that would further alienate myself from the people in this city. Suggestions??
— Shannon, Astoria, N.Y.

SG: Shannon, you’re my hero. I ran this by my unofficial Mailbag Committee (my buddies House, JackO, Wildes, Jacoby, Rydholm and Connor, and yes, I have elections every year to fill those seats because tough mailbag questions deserve that kind of commitment), and we came up with three options for you (that could actually be printed).

Runner-Up No. 1: Plaxico Burress
Just buy a Plax jersey online, cover your right leg in fake blood, then limp around while holding a fake gun for four hours.

2011 Update: This still works! It’s timeless!

Runner-Up No. 2: Bernie Madoff supporter
Make a big “FREE BERNIE MADOFF!” sign with a matching T-shirt, then walk around screaming “Free Madoff” chants until they kick you out.

Runner-Up No. 3: Eliot Spitzer and Ashley Dupre
But with a twist because you won’t go skanky: You dress up like Spitzer (nice suit, bald wig) and get one of your male friends (preferably someone who’s overweight and/or hairy) to cram himself into a call girl’s cocktail dress as Dupree.

Winner: Derek Cheater
Buy a Jeter jersey, cross out the “J” and write “CH” over it. Then buy a bunch of fake syringes and stick them into various parts of your body. And carry a big fake bottle that says “STEROIDS” on it, but fill it with Altoids. Then, walk around all night introducing yourself as “Derek Cheater.” This is my favorite idea because not only is it funny but Jeter has such a good reputation, and it’s so preposterous that he’d ever cheat — really, he’s one of the top-three picks in any “Which Guy From the ’90s and ’00s Definitely Didn’t Cheat” draft — that your costume would get a wide range of reactions ranging from “perplexed” to “truly ticked off,” and people might even yell at you and stuff. Also, you’ll definitely have your choice of romantic suitors because half the guys there will want to have hate sex with the girl brazen enough to wear a “Derek Cheater” costume to a New York Halloween party. Best of luck.

2010

Q: Am I the only one who wants to see 20,000 Cleveland fans with fake knives stuck on their backs when LeBron arrives in his new Miami uniform next year?
— Avi, San Francisco

SG: At the very least, it’s going to make for a fantastic Halloween costume: Take your LeBron Cavs jersey you don’t need anymore, pour some fake blood on the back, tape a knife handle on it and you’re good to go. Voila! Instant 2010-11 Cavaliers fan.

2011 Update: Still a winner.

Q: I want to dress up as Bill Simmons for Halloween. Can you give me some tips (dress, etc.) so I can make it as authentic as possible? I have been practicing the nasally voice for last several months so have that down pat. Thanks for the help!
— Jeff A., NYC

SG: I asked my wife to answer this question. Here’s what she wrote:

“Wardrobe: Broken-in jeans (frayed at the hem) worn falling down in the rear; wrinkled, vintage Red Sox T-shirt with NOTHING on the back and a coffee or nondescript food stain on the front; zip-navy hooded sweatshirt unzipped; Chuck Taylors; Fred Lynn baseball card in wallet along with at least $300 and 30 extra cards and business cards that you don’t need; hair like the late JFK Jr., but with silver highlights; blue/green contacts if you don’t have Bill’s dreamy eyes; he also has giant saucer eyes, so walk around with your eyes wide open like you’re in shock.

“How to carry yourself: Hold a BlackBerry in your hand at all times with e-mail or Twitter screen open and glance at it a lot; pretend to pay attention to your kids unless they need something, then act distracted like you just got an important e-mail; every 20 minutes, answer your phone and have an annoying basketball or football conversation with someone in a loud voice; if there’s a TV in the room showing a game, leave conversations mid-conversation and walk over to it to ‘catch the score’ even if it’s totally rude. Finally, Bill has no ass so I don’t know how you make that part of the costume. Maybe tape your buttocks so that they are inverted? Good luck.”

2011

I will unveil my Halloween costume picks in Friday’s NFL column. In the meantime, send Sarah Larimer and the Triangle staff your costume ideas already.

Bill Simmons is the Editor in Chief of Grantland and the author of the recent New York Times no. 1 best-seller The Book of Basketball, now out in paperback with new material and a revised Hall of Fame Pyramid. For every Simmons column and podcast, log on to Grantland. Follow him on Twitter and check out his new home on Facebook.

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