Classic Billboard Music Awards: The 90s

1990: Wilson Phillips

"Hold On" remains one of my favorite karaoke jams. Chynna has a Madonna-as-matador outfit vibe here that I had not recalled from her. Carnie is working the red suit but the Cleopatra hair is a little severe on her. Wendy just seems happy to be there.

1990: Janet Jackson

And Miss Jackson also wore a bra top. I didn't remember those were such hot commodities in 1990.

1990: Phil Collins

This is Phil and his wife, Jill Collins. One of their children is actress Lily Collins. So basically they're Phil and Jill and Lil.

1990: Alannah Myles

I totally bought her album just to own "Black Velvet." That's what we olds did back then, children. We bought entire cassette tapes full of songs we may never even have heard, just so we didn't have to wait to catch our favorite one on the radio. Alannah is serving up real Julianna Marguiles vibes here, not that we would have known that in 1990.

1990: Nelson

It's Nelson! Matthew and Gunnar! Or Gunnar and Matthew! They are the Property Brothers of music. I cannot live without their love and affection.

I guess this is their entire band? Or just their crew? Please make note of GunnerMatthew's leather chaps, but do not sleep on the BLUE SUEDE KNEE-HIGH SPATS next to him. Those are magnificently intense and I hope that man still has them. J.Lo might want to borrow them.

1991: Vanessa L. Williams

She is working this with adorable Seventeen magazine flair.

1991: Mariah

SO MANY fresh celebs in this era came to things like you would a dance in your sophomore year of high school.

1991: C&C Music Factory

#FreeTheNipple

1991: LL Cool J

I appreciate that he's posing for this as if it might, MIGHT, become an album cover.

1992: TLC

I assume they made these the night before, after raiding Charles Barkley's closet.

1992

It didn't work out so well for Left Eye, who lost her drawers mid-celebration.

1992: Heather Locklear

I totally forgot she was (at this time) married to Tommy Lee, whose union with Pamela Anderson has eclipsed all others for me, apparently. They got divorced a year after this, which is also right in between the Dynasty reunion movie and her arrival on Melrose Place. This outfit is too obviously vixenish for Amanda Woodward, but truly encapsulates the Nighttime Soap Villainess spirit.

1992 Billy Ray Cyrus

Do not become so fixated on the tailcoat and jeans that you overlook the fact that IT APPEARS the pants lace up the sides.

1993: Drew Barrymore

Now we know whose hair was on Donna Martin's mood board.

1993: Whitney and Bobby

Is this a pairs skate?

1993: RuPaul

Ever fierce, forever fierce.

1994: RDJ and Sheryl Crow

When I saw this, I was like, "Did they DATE???" Apparently not (he was recently married at this time, I believe). Sheryl's suit fits way better than his does, though, so I hope she did give him the digits... of her tailor.

1995: Shania Twain

Of course. This all tracks.

1995: Lil' Kim, Biggie, and Puffy (as he was then known)

This truly IS a time capsule.

1995: Faith Hill

See? High school dance. Faith FOR SURE looks like she's very excited about Prom.

1995: Salt-n-Pepa

I guess Salt's pants weren't finished in time.

1995: Mary J Blige

I didn't know she had a Catwoman phase.

1996: Mariah Carey

Did she tuck that up herself to make the slit?

1996: Toni Braxton

That's a wee snug, but she looks great in it nonetheless. It'd still work.

1996: Celine Dion

So would this, although it's not nearly kooky enough. She'd need to wear this with a 10-foot hat brim.

1997: Gwen

When your development exec comes back from a six month sabbatical on which she says she found herself.

1997: Meredith Brooks

She's a bitch! She's a lover! She's a child! She's a mother! She's a sinner, she's a saint, she does not feel afraid of brown velvet.

1997: Puff Daddy

I feel like all he wears now is a tuxedo, so this was a shock to the memory banks. I cannot imagine the Diddy of today dressing like he wants to do any outdoor activity.

1997: The Spice Girls

There's a lot to zero in on here, but me, I'm landing on Baby's and Scary's shoes. Although I AM confused why Ginger is dressed here as if she is attempting county fair cosplay.

1997: Busta Rhymes

Busta really believes in layers.

1998: NSYNC

I laugh every time I see their old photos. Every. time.

1998: Tori and the BAG

Again: I laugh every time I see old pics of Brian Austin Green. EVERY. TIME.

1998: Fergie

She was present with her band Wild Orchid, which played the Peach Pit After Dark at some point (probably this season). She appears to have turned a scarf into gloves? I kind of miss Fergie Ferg. The Black Eyed Peas played the VMAs without her and she was sorely needed.

1998: Natalie Imbruglia

That haircut is great on her. Is the rest dressy enough? I'm -- wait for it -- torn. (I am basic so here is where I say that is a seriously good pop song and I enjoy it, and maybe that's because I've had time and space from the era when it was on the radio every three seconds.)