The Final Moments of Rupert Roo...

SPOILER:If you’ve never seen the movie The Perfect Storm, serious details are revealed ahead! Additionally, this uses extreme language and is RATED 'R'. Proceed at your own risk.

Not too much on TV at 4am, even w/ Comcastic Video on Demand. I settled on The Perfect Storm, which has a decent soundtrack and good acting from John C. Reilly and William Fichtner. It’s about some East Coast fishermen who seek fortune from a big score (catching lots of fish) during a massive storm that threatens the lives of all on board. Here’s the end of it:They die. The storm causes the boat to capsize and all the men drown to death.

Summary:Guys go fishing, storm comes, storm tips the boat over and everyone dies. That’s about it. The characters are fleshed out a bit but that's the gist of it. And it really happened. The ruggedly handsome captain played by George Clooney was a real dude (only I bet he looked a lot more like Steve Buscemi than Dr. Ross). The only true detail known is that the ship went into a storm and disappeared. The actual boat and all of the bodies were never recovered.

Amazingly the writers of this screenplay determined that there was a shark attack and a stunning rescue of a man thrown overboard. Somehow they were able to fill in the hours and hours of mind-numbing sailing w/ interesting and quasi-complex storylines. But no one really understands what happened. For all they know, those men sailed out to sea to get away from their wives and hold a fierce Guitar Hero tournament.

I told a good friend that if I ever disappeared under mysterious circumstances that this was the most likely scenario:

Rupert Roo was newly released from the hospital after donating a kidney to a dying child when he met up w/ President Obama for sushi. During his hospitalization, Rupert had drafted a peace plan for the Middle East, learned to reverse global warming and mastered cold fusion. Later he met up w/ Scarlett Johansson and Salma Hayek. During a furious ménage a trois, Rupert (now w/ only one kidney) suffered a severe, anoxic event upon achieving full erection of his torrid, 24" penis. In an altered mental state from lack of blood flow and oxygen to his brain, Roo left the 2 women in post-multiple orgasm catatonia and stumbled outside. He staggered to Lake Michigan in a stupor and walked into the water, never to be heard from or seen again.

To which my friend replied:

Rupert Roo spent a night at his favorite club The Manhole, when he abruptly left the hotspot w/ suspicious scuff marks on his knees and watery eyes. He stabbed a homeless man in the throat on the way to his smack dealer when he remembered that it was his turn at the Gloryhole. This was no club, it was an actual gloryhole. After 2-3 hours of straight skull-fucking (actually, gay skull-fucking), the neurosyphilis that had been festering since he raped his first young boy during a grade school sleepover, kicked in. This infection caused acute confusion. In an altered state he stood up, wiped the most recent batch of jizz from his hair and marched his raging 2" boner into Lake Michigan, never to be heard from or seen again.

Which version do you think would make a better film, assuming I could get Mark Wahlberg to play the ‘Rupert’ character?

Best Emails Sent to Rupert Roo

I get a lot of neat emails that provide feedback and inspiration. BTW, if you recognize one of these quotes as something you sent me, either:
1.Thanks a lot, it was great to hear from you OR...

2.Go suck a dick

It should be evident which salutation is intended for you. Here are some of the classics.

1.“I cant believe that your really a doctor. I would never want to see a horribul person like you!”
Would you believe that I’m your 1st grade English teacher? And I’m flunking your dumb ass for such shitty grammar. I don’t know your educational background but your writing rivals mine when I was 12 y/o (and I have samples on this very site to prove it). Besides, I would never want to see a stoopid person like you.

2.“…weird that you tend to focus on the male penis in a lot of your posts.” “…for someone with dick on his mind all the time, I’m starting to think that you’re gay.”
First of all, it’s certainly less weird than if I wrote about the female penis. And secondly, since I am neither extremely happy nor homosexual, I’m not really sure what you mean. I’ve written about how I still laugh at low brow humor like the fart scene in Dumb and Dumber. This amusement does not preclude me from being a straight, intelligent and complex person. Dick jokes will always hold a special place in my heart, and probably in your cock-starved mouth, as well.

3.“That was a pretty gross post. You’re betting that people want to read about a grown man shitting himself?”
Yes, in fact I’ve bet my entire family fortune on http://www.grownmanshitting.com/. Please visit and click on a link, if you can (I get like 1/15th of a penny for every hit). Seriously, I put a disclaimer before all material that is borderline. Beyond that, the onus is on you.


"If you have no critics you'll likely have no success." -Malcolm X

4.“Keep up the good work Rupert. I showed this to my co-worker and we both died laughing.” (This was after my post called “Conversation with a Stripper”, so I’m wondering where these guys worked)

Thanks for the nice email. I’m not used to getting kind praise in my inbox, outside of Facebook comments from friends or family. So this was a pleasant change.

5.“If I see you write the word reta** one more time, I’m going to trace your ISP, go to your home and kick your fucking face in!”
That’s more like it! I’ve gotten very used to this kind of post. It’s my bread and butter, baby.

6.Preface: I’d written something like, 'I’m somewhat afraid to honestly write my thoughts on this subject..etc.' “You should be afraid to write garbage like that. Keep going and see what happens to you.”
Dude, in my brief 30 yrs I’ve broken my neck, been held up at gun point, grabbed a man’s heart in my hand and manually induced beats to keep him alive, gotten knocked unconscious in a fight, entrenched $200,000 in debt, watched Waterworld, witnessed many sick people die right in front of me and had 3 car accidents. An anonymous threat over the Internet doesn’t scare me. Plus I’m like 6’6 and 280 lb. And I know Brazilian Jiu-Jitsu.

7.“You probably don’t remember me but I think we grew up together. Are you the same Rupert Roo who went to Pisgah High School in Rantkin County?”

Wow! I don’t know what’s more incredible: that someone really did name their kid “Rupert Roo” or that there's a high school called “Pisgah”? Did you attend Pisgah Middle School? If so, did the basketball team and cheerleaders have “PMS” written on the front of their uniform? I couldn’t resist. Honestly, Rupert is not my real name.

Like Bruce Wayne or Peter Parker, I need to protect my loved ones. Unlike them, I do not fight crime and improve society at large. At least not as far as you know. Thanks for writing, including the negative stuff. You guys keep me honest. Please continue to do so.

Embarrassing Alcohol Story #19.5b

Note:This is a true and tragically graphic story, proceed at your own risk.

My roommate through most of med school was an interesting guy. Let’s call him Brad. One of the areas Brad excelled in was women, and he earned the nickname “The Jewish Wilt Chamberlain” for his efforts. He took on the Herculean task of providing new college girls w/ sexual orientation (introducing them to toys, pubic landscaping and how to get off in general).

One random Saturday morning I was checking cnn.com when he came stumbling in at 9am, reeking of cheap alcohol and a Port-O-Potty. He made his way into the bathroom, where more stumbling was audible: “You ok, man?” I asked.

“Dude, you won’t believe the night I just had….”

Brad had met up w/ 2 undergrad girls from the local college the previous night. Being the mench that he was, he planned on expanding their curriculum. Note that he was 30y/o and I was 24. Best guess is that these girls were 19. As the smooth talking Hebrew, he convinced these coeds to invite him and a giant bottle of Tequila over to their apt for a night of debauchery.

The evening started out with a few drinks and an occasional bong hit, pretty standard... actually. Brad possessed a ginormous alcohol tolerance and suggested that they play card games w/ the loser having to pound shots of Patron in hopes of quickly intoxicating his female hosts. But the poker Gods did not favor this plan and Brad lost nearly all the games that were played.

The end result of this strategy was a ½ empty carafe of tequila, 2 horny college chicks and my roommate too drunk to do anything about it. Aside from finishing the other half of the tequila bottle, the remaining details of the night were not very clear. Apparently an anonymous, foul-smelling college frat boy showed up to drink and smoke up w/ them as the evening progressed. At some premature time, Brad passed out with his face to the floor. Frank the tank, indeed.

He awoke around 5am, still drunk and disoriented. The smell of a diaper changing station filled the apartment. Brad lifted his head to see the frat boy passed out on the couch. That frat boy was farting up a fucking shit storm! Deciding against spooning with the malodorous college kid, Brad turned on his side to resume his slumber.

A 2nd time he awoke to whispers of the girls and a still lingering, but diminished scent of the college boy’s stale farts as the morning sun heated the room. The whispers quieted and Brad heard the voices leave the apt. College boy had vacated the couch so Brad quickly stole his spot. He slept there for another 2hrs. When he woke up this last time he felt something cold and itchy in his pants. Reaching down to scratch his ass my roomma-

“No way!” He said out loud. “No… Fucking…. Way!”

Then it hit Brad like that moment in The Sixth Sense when Bruce Willis realizes he’s actually dead: The whispers from the girls, the overpowering stench of a baby’s fresh diaper. And just like when Willis notices the bullet wound in his abdomen w/ blood spilling out of his back, Brad looked down in absolute horror to see a giant brown skid mark on the seat of his pants extending south toward his ankle and continuously leaking onto the floor and couch.

My roommate sprinted to the bathroom and took off his boxers, which apparently did resemble a dirty, cloth diaper only much colder. He wiped his filthy ass the best he could and then put his shit-stained jeans back on commando style.

“I just wanted to have a threesome w/ those college girls!” Brad shouted to me from the shower. No good deed, right?

Conversation with a 12y/o Me Plus Some Hot Chicks

The following is a conversation w/ my 12 year-old self from the year 1990. In the end our talks centered mostly on my TV-addicted salad days (more like Chips A’Hoy, Fruit Funs and Dr. Pepper days) and how they made me the man that I am today.

Me:Here I am w/ my 12 year-old counterpart, also Rupert Roo, straight from 1990.

12y/o Roo:Holy crap! You’re me from the future?

Me:Yup.

12y/o Roo:How come my voice is still so high?

Me:It is not!

12y/o Roo:See, it just got high again, right there!

Me:Moving on… I wanted to give you, the 12 year-old version of me, the chance to ask anything about the future. We can talk about business, politics, the global sta-

12y/o Roo:What year do the Cubs start their dynasty of winning 5 World Series in a row?

Me:Actually that doesn’t happen. It’s been over 100 yrs now and they still haven’t won a single championship. They almost made it in 2003 but Florida beat them.

12y/o Roo:Weak, man.. Bogus… Florida…Florida???

Me:Anything else you want to know about the future?

12y/o Roo:What kind of flying car do I drive?

Me:Uhh none. You take the subway, and no, the subway doesn’t have flying cars, either.

12y/o Roo:This sucks! Is there anything cool about the future at all?

Me:Well this might cheer you up. A lot of the cute child stars that you watch on TV now grow up to be super hot.

12y/o Roo:Really, like who?

Me:Let’s take a look, 12 year-old Rupert! And keep your hands where I can see them. Remember, I know what you do w/ those Sunday JC Penney ads when no one else is around.

1.Ashley Banks
Me:Pass the malaria meds, cuz I gots me some Jungle Fever!

12y/o Roo:What does that mean?

Me:Spike Lee will explain it in a yr or two.

2.Lacey Chabret from Party of Five
12 y/o Roo:I always thought that Jennifer Love Hewitt would grow up to be the hot one.

Me:No, she makes two Garfield movies and a TV show about whispering shit to ghosts.

12 y/o Roo:Why are ghosts whispering shit to the chick from Party of Five?

Me:I don’t know. In the future whispering is also the preferred mode of communication b/w most dogs and Mexicans.

12 y/o Roo:Weird.

3.Punky Brewster
12y/o Roo:Why does her face look all funny?

Me:She’s had a lot of work done.

12y/o Roo:That’s why I don’t want to work hard when I grow up.

4.Nicole Eggert from Charles in Charge

12y/o Roo:
I figured she would grow up to be hot. I'm 12 and as I look at her I think, “Boy, she’s gonna be hot some day”.

Me:I feel the same way about Hermione Granger right now.

12 y/o Roo:You are a sick, sick man.

Me:I know.

5.Topanga
12y/o Roo:Why are her lips all puffy?

Me:It’s an allergic reaction.

12 y/o Roo:To what, seafood?

Me:No, to type A Botulinum toxin.

6.Stephanie Tanner
Me:How do you like those Olsen twins?

12 y/o Roo:How rude!

7.Fergie from Kids Incorporated
12 y/o Roo:I thought she would end up in movies.

Me:No. No drama. No, no, no, no drama, drama.

8.Alyssa Milano
12 y/o Roo:I would murder my own mother for one night with her.

Me:And you do in an odd deal w/ a Paraguayan pimp in the August of ‘99.

12 y/o Roo:What?!?

Me:Nothing...

9.Anyone on the “New Mickey Mouse Club”
Me:Britney, Christina and the chick from Felicity all started out there.

12 y/o me:Yeah, too bad they had to work with fags like Justin Timberlake and Ryan Gosling. Who’d ever want to be with those queermos?

Me:Yeah.. uhm.. your homophobic slurs aren’t nearly as appreciated in 2008 as in 1990.

12 y/o Roo:Ok, gayrod.

10.Winnie Cooper

12y/o Roo:I always wanted a girl like Winnie Cooper in my life as I grew up.

Me:Yeah, but you looked a lot more like Paul Pfeiffer than Kevin Arnold, so you didn’t.

12y/o Roo:Fuck off!

Me:You just told yourself to fuck off, retard.

12 y/o Roo:Whatever happened to Kimberly Drummond? She was pretty hot.

Me:She uhh… she has her own variety shown on cable.

12 y/o Roo:And I can’t wait to hear the new music that Michael Jackson makes! I even have a poster of Michael on my wall that says, “BEAT IT!” in big letters.

Me:Oohhh yeah, I forgot that poster. You’re gonna want to take that one down.

12 y/o Roo:What? Oh I get it, you can’t tell me. It’s a space-time continuum kinda thing, huh?

Me:And stop talking like that, it’ll only delay what becomes a painfully prolonged virginity.

12 y/o Roo:Ok. I guess I’ll just have to wait for 2008 when I am CEO of Rupert-Tech industries, have 12 dogs plus my own monkey and live in a super mansion, right? That is what happens, isn’t it?