17 Awkward Magazine Covers From The '90s & Early '00s That Will Make Your Day

You have to love those special years that were the late '90s and the early '00s — celebrity gossip was at its very peak, boy bands were all the rage, and people still referred to Lindsay Lohan as a "star on the rise." Of course, now that it's 2014, some of the magazine covers from back in the day now feel just a touch awkward, and I'm not just talking about any early '00s photo of NSYNC. Whether it's the completely ridiculous photo or cringeworthy tagline, check out the magazine covers that will make realize how great and ridiculous this time in pop culture history really was.

by Kaitlin Reilly

Awkward Cover #1

Remember Oprah’s wedding? Oh, right.

Image: People Magazine

Awkward Cover #2

The cut-and-pasted photo of Destiny’s Child is almost as awkward as the string of words attempting to form an edgy caption.

Image: Vibe

Awkward Cover #3

I’m not sure whether Claire Danes is supposed to represent the “guy magnet” article or the “why I joined a cult” one, but the dead expression in her eyes is hinting at the latter.

Image: Seventeen

Awkward Cover #4

HIStory. Get it? Because it’s Michael Jackson’s STORY!

Awkward Cover #5

The Clockwork Orange cover should be cooler than it is. Eminem just looks drunk.

Image: Spin

Awkward Cover #6

Titanic 2? No. Not a thing.

Awkward Cover #7

…Did Nickelodeon Magazine just call Tim Allen a tool?

Image: Nickelodeon Magazine

Awkward Cover #8

Just try explaining this cover to kids born before 1995.

Image: Hello!

Awkward Cover #9

This pun was inevitable. The flaming words were not. Be better, Maxim.

Image: Maxim

Awkward Cover #10

I don’t know what’s more uncomfortable to look at, Rob Lowe’s singular diamond stud or his concave stomach.

Image: People Magazine

Awkward Cover #11

Seems pretty average until you realize that we’re going to learn and David Boreanaz’s favorite body parts.

Image: Seventeen Magazine

Awkward Cover #12

Is “Diet Wars” some sort of prequel to The Hunger Games? Don’t bring Oprah into this.

Image: People Magazine

Awkward Cover #13

Literally the laziest pun in the entire world.

Image: Nickelodeon Magazine

Awkward Cover #14

I wish I could tell you why Brad Pitt is wearing a sheath dress. I really wish I could tell you.

Image: Rolling Stone

Awkward Cover #15

This was one of Britney Spears’ first overtly sexy photoshoots, and the fact that she is posed as a child lying on her bed with a Teletubby is highly disturbing.

Image: Rolling Stone

Awkward Cover #16

Umm, yeah. Maybe you shouldn’t party like this celebrity.

Image: CosmoGirl

Awkward Cover #17

LOL at Pink’s hair and the fact that YM called a bunch of artists we no longer care about “tasty morsels.”

Image: YM