Michelle Bombshell: May 19, 2010
Bombshell covers more parts of her body than have ever before been covered at the same time, but ends up looking a streetwalker version of Elvira. Here is a quote from the accompanying article:

Now I think men are made to spread their seed. Women need to accept that. If you're going to be married to somebody, you need to know that men are not meant to be with one woman.

As for Sandra Bullock,

I'd like to sit down and talk to her over lunch. I don't expect that she would do it though.

Hailey Glassman: February 17, 2010
This is the greatest Steppin' Out cover of all time, depicting Jon Gosselin ex Hailey Glassman—styled, presumably, by Noah Cyrus. See the the fingerless black leather gloves on Hailey's hands. See her hot pink lace panties and leopard-print boob swaddle. See the invitation to judge. Here is a excerpt from her interview:

[Jon Gosselin] was so small I didn't think he would cheat on me. He's hung like a nine-year-old boy.... It's so tiny, tiny, tiny.

Tila Tequila: May something-or-other, 2010
I think this is the May 12 issue, but there's no date on it. It celebrates the launch of Tila Tequila's gossip website, TilaTequilaOMG.com, which is also where I found it. Anyway, we're fans of this one because our website got name-checked underneath Tila's crotch. There is no prouder place in journalism than inches from Tila Tequila's left labia.

Jerry Springer: April 22, 2009
Sometimes Steppin' Out is forced to feature people who are not boobalicious females. When this happens, Chaunce wanders over to his favorite strip club, Scores, grabs the first barely legal naked thing he sees, throws her in a Steppin' Out t-shirt and—bam!—instant cover. Wait, who was this cover supposed to be about, again? Oh yeah, Jerry Springer. We'll add his face post-production.

Tatum O'Neal: June 3, 2008
The day of Tatum O'Neal's crack bust was the luckiest day in Steppin' Out history. By coincidence, Tatum had just giving an interview to Steppin' Out about how she was "in a good place." So they ran the interview and Tatum's cover, and it was like their headlines were ripped from the headlines, but inverted and upside down.

Kari Ann Peniche: December 24, 2008
Oh, this girl's face is familiar, how do we know her again? Oh yeah, the third person from the Rebecca Gayheart - Eric Dane naked video.

Amy Fisher: February 27, 2008
Amy "Long Island Lolita" Fisher earned her fame as a Long Island teenager who shot her much older lover's wife. Her Steppin' Out issue caused her to complain, "You obviously wanted to make me look really bad... You made me out to be a monster and I'm not and you know it."

Jersey Shore: December 30, 2009
Steppin' Out nearly burst into flames when this perfect storm of Jersey occurred.

Shannon James: January 28, 2009
Apparently, Shannon James was a Playboy centerfold. Apparently, she uses the same stylist as Hailey Glassman. Unless, of course, gals in the Playboy mansion regularly belt shimmer scarves over their underwear, I'm not sure, but you could probably find out by watching The Girls Next Door.

Courtney Friel: May 2, 2007
Fox News reporter, beauty queen, and fancy closet haver Courtney Friel had a Steppin' Out cover? This could ruin her reputation!

Jenna Jameson & Tito Ortiz: December 27, 2006
It is testament to how poorly these two lives have gone that they look way better on this cover than they do now in real life. My favorite thing about this issue is the parenthetical note that Natasha Yi is (stunning).

Sunset Tan: November 26, 2008
The cast of a tanning salon reality show romp and undress one another, a mysterious disembodied hand reaching for one comely female's sloppy right breast. Steppin' Out: the disembodied hand always reaching for America's sloppy right breast.

Thanks, Chaunce Hayden. That was fun. Send us an early PDF of your next issue?

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