NSFW November: Cara Wakelin, Miss November 1999

I am beginning to see a light at the end of the tunnel. This is the last Playmate post for today. Then four tomorrow, four Monday, the really fun final post for Tuesday in which I’m planning to crunch some of the gals’ numbers and do some trendspotting, and then I’m going to be forever done with the Miss Novembers. Whew!

The lovely and talented Cara Wakelin was Playboy’s Miss November 1999.

Photograph by Richard Fegley

That centerfold picture is largely garbage, poorly lit and ill-conceived, story-wise, just overall not as strong a composition as this project has lead me to expect from Fegley. Predictable and lacking a certain joy or playfulness. But this picture harkens back to vintage pin-up style, a great composition that is also freaking adorable!


When Cara’s mom read that the Playboy 2000 Playmate search bus was coming to their hometown of Toronto looking for new Playmates, she urged her hesitant daughter to go for a photo test. Thank goodness she did.” (“Catch of the Day,” Playboy, November 1999)

Q : This is your first modeling gig. How did your mother persuade you to try out for Playboy?
A : When she saw the newspaper article about the Playmate 2000 search, she started jumping up and down, saying, “You have to do this. You can do it.” I’ve never been very confident about my appearance. As we pulled into the parking lot, I saw ten beautiful blondes waiting in line. I said, “Mom, take me home. What am I doing here?” She said, “Cara, if you don’t get out of this car right now, I’m dragging you in there.”

Golf claps for Mrs. Wakelin, please, everyone? If you want to send her a fruit basket thanking her for her maternal powers of persuasion, airmail that shit to Canadialand, and mind you wrap it up nicely so it doesn’t get frostbitten. Do you all have even postal service up there in the icy North, or do you guys just tape your mail to a moose’s antlers, point him South, slap his ass, and hope for the best?

Besides making a cameo as the Princess in Death to Smoochy, one of my favorite movies, Ms. Wakelin also wins my love for appearing on an episode of the short-lived talk show of one of my all-time favorite athletes and a man who has always been in my top five list of People I Would Like to Be Stuck In An Elevator With: John McEnroe!! She was a guest on his show for one of the last episodes and appeared alongside wonderfully creepy gap-toothed comedian Paul Scheer.

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