Drew Barrymore: April 1994
So, this happened after Wayne's World 2 and The Amy Fisher Story, but before Boys On The Side and Batman Forever (and the Letterman flashing, which was 1995). Immediately striking: the HORRIBLE weird cover fonts. It looks like something rendered improperly. Also, I definitely want to know Heather Locklear's hair history. Was that as shocking as her hunk history?
Pink: April 2002
She looks like Anna Faris to me here. Also: Pink HAS, I think, asserted her longevity, not that anyone will ever forget Britney; "chicks who changed MTV" sounds like the kind of dumb dreck you'd see on Maxim; and is there ANY more 2002 cluster of It People than Ja Rule, Hoobastank, The Calling, and Quddus? HOOBASTANK. However, Internet rumors can still ruin lives, and obsessed fans ARE nuts, so some things will be true forever.
Jimmy Fallon, 2002
I don't know why this magazine exists differently than YM, but I mostly wanted to note that Jimmy Fallon is a FETUS here.
Brandon and Kelly, March 1992
Okay, it's March, not April, but CLOSE ENOUGH. This is how these two will forever exist in my head.
Gwen Stefani April 1997
Some of this language is SO Innocent Teen. "Cool" ways to make him your boyfriend is just so... young. As was Gwen, who if memory serves routinely wore a sparkling bindi with no thought to whether it was culturally appropriate. I am absolutely sure people were having those conversations in 1997; it's just that back then, it was a lot easier for those who needed to hear them to turn a deaf ear.
Omar Epps, Claire Danes, Giovanni Ribisi: April 1999
This cover has declined to name-check Omar Epps and Giovanni Ribisi entirely. It's also really terrible of all three of them, which... apparently the Mod Squad reboot they were promoting was equally terrible, so this turned out to be historically thematic. Ribisi genuinely looks like he's considering which of your internal organs to eat.
Mariah: April 1992
Look at that glorious hair. This magazine is full of mixed messages, also. Make him want you! Go super far! But don't do this one thing!
Johnny Depp, March 1988
Another March one. A terrible color scheme making your eyes bleed. And Johnny Depp's cheekbones, from back when we didn't know how all this was going to go.
O-Town: April of... probably 2001
I recapped this season of Making The Band for Television Without Pity (then Mighty Big TV) and this is basically the worst imaginable photo of all five of them except MAYBE Trevor in the middle there. Needless to say, I did not get down with the sexy free poster that was promised.
Grant Show and Andrew Shue, April 1993
MELROSE PLACE AHOY. I enjoy "Guess which one isn't wearing underwear" right over a headline about how guys lie to you. Maybe one of them is LYING about the underwear thing! I also don't love "what guys think of girls who have sex" because somehow I doubt the answer was in any way empowering.
Dawson's Creek, April of... something
I love the very notion that Leonardo DiCaprio is reduced to the tiny corner banner so that Dawson's Creek can own the cover. THIS WAS QUITE A TIME.