OMG GUYS! I HAD, LIKE, THE BEST MORNING, LIKE, EVER! I woke up pretty! Crazy, right?! Last night, I was laying down on newspapers and empty bottles of London dry in the alley, when I told myself: “Fuck this. I’m waking up pretty!” So I dreamed really hard. Like really hard. To make it come true. “Please be pretty. Please be pretty. I will do anything God. Suck anything. Just make me pretty.”
So I dreamed real hard.
And when I woke up the next day… it worked. I was super pretty. LIKE SUPER PRETTY. Like I had a completely new super pretty face! And let me tell you man, it was like the world was smiling at me. Disney bluebirds chirping in my ear as I walked down the streets. Every man and woman drooling over me, wanting to take a bite of this fine-ass sailor. My new pretty face had this power to control, like, everyone. Taxis were free. Dinner at SUR comp’d. Life as a beautiful person was glorious.
Back to reality: I’m not an attractive man. I’m not ugly. But I’m sure not Playmate of the Year pretty. But I bet it’s probably pretty amazing to be super beautiful. People adore you. People fornicate to you. People give you free shit all the time.
For instance… Playmate of the Year is like the holy grail of being crowned “Most Pretty.” The prestige and glamour of the title have launched huge careers and forged young boys into adulthood. One of the perks of being Playmate of the Year? the wheels. Since 1964, Playboy has given the lucky, very pretty winner a car and boy have they been a spectacular pair to see.
Here’s my 10 favorites from all of Playboy history. Note: Fast sexy cars painted pink are like way more cute. Second note: Porsche and Jaguar ruled the ’80s. Third note: I know nothing about cars. This list is all gut and libido, baby.
10. 1950 Chevrolet Pickup Truck
PLAYMATE: DALENE KURTIS (2002)
Leave it to a girl from Bakersfield to screw the Euro sports cars and get herself a pickup.
WHAT THE RIDE SAYS ABOUT HER: Dalene Kurtis is never far away from a cornfield and a red cup full of jungle juice.
9. 1985 Toyota MR2
PLAYMATE: KAREN VELEZ (1985)
I don’t even really like this car. But because Karen Velez had the insane idea to pick a Toyota over anything else… I applaud her.
WHAT THE RIDE SAYS ABOUT HER: I might be the only one in the world to own a 1985 Toyota sports car and I’m not sure if that’s a good thing or not.
8. 1993 Jaguar XJS
PLAYMATE: ANNA NICOLE SMITH (1993)
You can never go wrong with a Jaguar and a ’93 Anna Nicole.
WHAT THE RIDE SAYS ABOUT HER: I like my ride to be classy and glove compartment stocked with Red Bulls?
7. 1989 Porsche 911 Cabriolet
PLAYMATE: Kimberley Conrad (1989)
1989 was a good year for Alabama babe Kimberley Conrad. She became Playmate of the Year. Married Hugh Hefner. And also she received this sweet Porsche. Yep, the summer of ’89 was oh-so-glorious for Conrad (and us).
WHAT THE RIDE SAYS ABOUT HER: The ’80s were my bitch.
6. 1998 Shelby Series 1
PLAYMATE: KAREN MCDOUGAL (1998)
The only car built from the ground up by legendary American icon Carroll Shelby. Karen McDougal was voted #2 Hottest Playmate of the ’90s. This Shelby. This girl. A match made in heaven.
WHAT THE RIDE SAYS ABOUT HER: I’m built well from my toes to my nips.
5. 1975 Porsche 911S
PLAYMATE: MARILYN LANGE (1975)
Another glorious babe… Marilyn Lange shows us another glorious Porsche.
WHAT THE RIDE SAYS ABOUT HER: She prefers the 1975 movie Shampoo over Jaws.
4. 1969 Shelby GT500 Fastback, 428 Cobra Jet (Pink)
PLAYMATE: CONNIE KRESKI (1969)
This car looks fricken sweet. So does Connie Kreski.
WHAT THE RIDE SAYS ABOUT HER: Follow the disco ball light to one hell of an orgy.
3. 1972 DeTomaso Pantera
PLAYMATE: LIV LINDELAND (1972)
Norwegian babe, Liv Lindeland was the first playmate to show visible pubic hair. We all know how hairy the rest of the decade went. Also, the DeTomaso Pantera is the car Elvis shot a bullet at when it wouldn’t start.
WHAT THE RIDE SAYS ABOUT HER: I fucked fat Elvis in Vegas once.
2. 1999 Shelby CSX 4000 Series Cobra
PLAYMATE: HEATHER KOZAR (1999)
One of Barker’s Beauty models from the Price is Right. Heather Kozar‘s just about the only thing former Browns quarterback Tim Couch did right.
WHAT THE RIDE SAYS ABOUT HER: My husband is a shitty quarterback but my car fucks better than yours.
1. 1964 Ford Mustang Convertible (Pink)
PLAYMATE: DONNA MICHELLE (1964)
This car is the tits. This is the car that launched Mustang into the forefront of badassery in America. Donna Michelle is the first Playmate of the Year to get a car. You know what image gets my libido going: 1964, Donna Michelle in this Ford Mustang, ripping down Highway 1 listening to Orbison’s ’64 hit, “Oh, Pretty Woman.”
WHAT THE RIDE SAYS ABOUT HER: I’m an All-American classic, babe, so piss off.