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The 1999 American Music Awards Was The Most '90s Award Show Of The '90s

The 1999 American Music Awards was a summary of our time in the '90s. The internet was still in its infancy, record sales were still booming, and boybands ruled the world. If we had to create a time capsule to define our decades, this is the tape we should leave in there for the '90s, and here's why...

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Brandy and Melissa Joan Hart were the hosts.

Brandy was starring in Moesha, had a hit single ("Have You Ever?"), and was about to star in ABC's revitalization of the Wonderful World of Disney starring herself and Whitney Houston. Oh, she also starred in this AWESOME Movie of the Week with Diana Ross called "Double Platinum." The movie's amazing. And because the show's on ABC, they thought Sabrina the Teenage Witch was an appropriate co-host. She was.

Brandy was starring in Moesha, had a hit single ("Have You Ever?"), and was about to star in ABC's revitalization of the Wonderful World of Disney starring herself and Whitney Houston. Oh, she also starred in this AWESOME Movie of the Week with Diana Ross called "Double Platinum." The movie's amazing. And because the show's on ABC, they thought Sabrina the Teenage Witch was an appropriate co-host. She was.

They name dropped the following in their monologue...

Celine Dion sans the babies.

Celine Dion sans the babies.

Will and Jada...

Will and Jada...

LeAnn Rimes... and is that Casey Keegan?! I actually forgot that she and Andrew Keegan dated in the '90s. I'm sure that that information was in a BOP somewhere.

LeAnn Rimes... and is that Casey Keegan?! I actually forgot that she and Andrew Keegan dated in the '90s. I'm sure that that information was in a BOP somewhere.

The first award of the night went to Will Smith for "Big Willie Style." Will we ever hear of another hit single called "Big Willie Style" ever again? I'm thinking no, but I'm hoping yes.

The first award of the night went to Will Smith for "Big Willie Style." Will we ever hear of another hit single called "Big Willie Style" ever again? I'm thinking no, but I'm hoping yes.

Whitney Houston was the first performer...

She sings "Until You Come Back" in this nice coat and it's amazing because it's Whitney. Then she tosses the coat aside and Wyclef Jean comes along to sing "My Love Is Your Love" with her. It was amazing. Did I mention Babyface was playing the piano for her? Babyface.

She sings "Until You Come Back" in this nice coat and it's amazing because it's Whitney. Then she tosses the coat aside and Wyclef Jean comes along to sing "My Love Is Your Love" with her. It was amazing. Did I mention Babyface was playing the piano for her? Babyface.

This happened.

98 Degrees was so down with this jam.

98 Degrees was so down with this jam.

No, really. There they are.

You think I was lying? I have photographic evidence that it happened. There they are.

You think I was lying? I have photographic evidence that it happened. There they are.

*NSYNC and Monica presented.

These outfits were so '90s. I really can't forget them. They can't leave my head. So... much... pleather.

These outfits were so '90s. I really can't forget them. They can't leave my head. So... much... pleather.

Country Music Award went to...

Who the hell else would it go to? It's the '90s. Garth ruled the '90s.

Who the hell else would it go to? It's the '90s. Garth ruled the '90s.

Backstreet Boys performed and this happened?

I still can't tell whether it was staged or not but it was awkward as hell. They filmed almost the entire segment in slow motion and Brian was attacked in slow motion. They sang "All I Have To Give" and their new single "Backstreet's Back." They never went away so I don't know where they went, but they're back.

I still can't tell whether it was staged or not but it was awkward as hell. They filmed almost the entire segment in slow motion and Brian was attacked in slow motion. They sang "All I Have To Give" and their new single "Backstreet's Back." They never went away so I don't know where they went, but they're back.

Deborah Cox and Isaac Hayes were presenters.

There were a lot of Canadians at this show. Deborah, Celine... what other Canadians will we run into? Also, metallic clothing was very, very in back then. The '90s loved being shiny.

There were a lot of Canadians at this show. Deborah, Celine... what other Canadians will we run into? Also, metallic clothing was very, very in back then. The '90s loved being shiny.

Another Canadian (and of course this song won)!

Best Adult Contemporary was Backstreet Boys, Celine Dion, and Shania Twain. This category can't get any more '90s, actually. But Titanic was the biggest movie of all time so... of course she won. I even bought the album! I listened to it while doing homework. Titanic forever!

Best Adult Contemporary was Backstreet Boys, Celine Dion, and Shania Twain. This category can't get any more '90s, actually. But Titanic was the biggest movie of all time so... of course she won. I even bought the album! I listened to it while doing homework. Titanic forever!

The Dixie Chicks performed and they were up for Best New Artist.

They also wore those outfits. Cheetah print and plastic-looking, metallic, hot colors? Oh, yeah. Those were so in. Why?! I CAN'T EVEN REMEMBER.

They also wore those outfits. Cheetah print and plastic-looking, metallic, hot colors? Oh, yeah. Those were so in. Why?! I CAN'T EVEN REMEMBER.

Freddie Prinze Jr. and Tatyana Ali? Sure.

Freddie was a total heartthrob teen idol of the '90s. "I Know What You Did Last Summer" and "She's All That"? Oh, yeah. Huge hits in the teen world. Tatyana Ali was done with Fresh Prince but do you guys remember she was a pop star? I sure do!

Freddie was a total heartthrob teen idol of the '90s. "I Know What You Did Last Summer" and "She's All That"? Oh, yeah. Huge hits in the teen world. Tatyana Ali was done with Fresh Prince but do you guys remember she was a pop star? I sure do!

Master P won for Best Rap Artist.

And he won wearing this outfit. This? All this? It was hip. Just remember, kids, fashion is cyclical. This might be coming back in your kids' generation.

And he won wearing this outfit. This? All this? It was hip. Just remember, kids, fashion is cyclical. This might be coming back in your kids' generation.

3EB performed!

"Who?!" you ask. On the screen was 3EB and I didn't know who that was until I see Stephan Jenkins standing in the middle of the stage in those zebra-print pants. Why did we want to see animal skin on our pleather pants so badly? The cameras also thought they were being "artistic" by not holding still for two seconds kind of reminiscent of those cartoons that would give children seizures.

"Who?!" you ask. On the screen was 3EB and I didn't know who that was until I see Stephan Jenkins standing in the middle of the stage in those zebra-print pants. Why did we want to see animal skin on our pleather pants so badly? The cameras also thought they were being "artistic" by not holding still for two seconds kind of reminiscent of those cartoons that would give children seizures.

LeAnn Rimes and Angel.

No, seriously. Does he or does he not look like Angel on this television show where he's supposed to be David Boreanaz? He also looks like he wants to be anywhere else but standing right there.

No, seriously. Does he or does he not look like Angel on this television show where he's supposed to be David Boreanaz? He also looks like he wants to be anywhere else but standing right there.

Alabama was the most popular country group!

All I know about Alabama is 1999 was the year they recorded that duet with *NSYNC, re-recording "God Must've Spent" with them. Sorry, country fans. But, hey! They won! Yay!

All I know about Alabama is 1999 was the year they recorded that duet with *NSYNC, re-recording "God Must've Spent" with them. Sorry, country fans. But, hey! They won! Yay!

K-CI & JOJO PERFORMED WITH NEXT.

LET ME REPEAT THAT: K-CI & JOJO ("ALL MY LIFE") PERFORMED WITH NEXT ("TOO CLOSE"). YOU CANNOT GET ANY MORE '90S THAN THAT RIGHT THERE. NOPE.

LET ME REPEAT THAT: K-CI & JOJO ("ALL MY LIFE") PERFORMED WITH NEXT ("TOO CLOSE"). YOU CANNOT GET ANY MORE '90S THAN THAT RIGHT THERE. NOPE.

(Some band) & Sinbad.

This was a popular country duo. Google tells me they're The Kinleys. So. There you go. Next to Sinbad who seems judgy about their outfit choices.

This was a popular country duo. Google tells me they're The Kinleys. So. There you go. Next to Sinbad who seems judgy about their outfit choices.

Pop/Rock New Artist went to...

They hugged real tight.

Chris and Lance's bear hug is giving me so many feels right now.

Chris and Lance's bear hug is giving me so many feels right now.

They accepted their award in these outfits.

Oh, Joseph. What's going on here? I did love how each one of them spoke in the acceptance speech. Equal players in this group. Justin's wearing some blue puffy things. Those puffy jackets were so in.

Oh, Joseph. What's going on here? I did love how each one of them spoke in the acceptance speech. Equal players in this group. Justin's wearing some blue puffy things. Those puffy jackets were so in.

Everclear and Faith Evans?

I am not understanding these cross genre presenters.

I am not understanding these cross genre presenters.

SPEAKING OF CROSSING GENRES...

This is Coolio performing with Blondie. Debbie Harry decided to do an interpretive dance while rappers sang around her. Look, this performance was ahead of its time. Now it's Eminem and Elton John, Eminem and Rihanna... just Eminem.

This is Coolio performing with Blondie. Debbie Harry decided to do an interpretive dance while rappers sang around her. Look, this performance was ahead of its time. Now it's Eminem and Elton John, Eminem and Rihanna... just Eminem.

Garth Brooks and his signature hat...

... were there to pay tribute to Billy Joel and Billy Joel's career because 1999 seemed like a great time for that. And the following performers played a medley of his hits and changed all the lyrics so they related to Billy Joel! It's just as weird as it sounds.

... were there to pay tribute to Billy Joel and Billy Joel's career because 1999 seemed like a great time for that. And the following performers played a medley of his hits and changed all the lyrics so they related to Billy Joel! It's just as weird as it sounds.

Brian McKnight...

... slayed "Piano Man" and this very much pleased Billy.

... slayed "Piano Man" and this very much pleased Billy.

98 Degrees...

... got "Uptown Girl."

... got "Uptown Girl."

Shawn Mullins...

... got "Allentown." Also, Shawn Mullins happened in the '90s.

... got "Allentown." Also, Shawn Mullins happened in the '90s.

*NSYNC...

... sang "You May Be Right" and didn't change any of the lyrics. Wtf, AMAs? Why ruin the pattern?

... sang "You May Be Right" and didn't change any of the lyrics. Wtf, AMAs? Why ruin the pattern?

"Just the Way You Are" also got to keep all its lyrics. Why?!

"Just the Way You Are" also got to keep all its lyrics. Why?!

Billy Joel accepted his award...

... and pretty much looked like, "Hey, it's way too early for me to receive this award." I agree, Billy. I agree.

... and pretty much looked like, "Hey, it's way too early for me to receive this award." I agree, Billy. I agree.

Brandy had a hit, hit song.

She sang "Have You Ever?" and had a costume change before going back to her hosting duties. She helmed Cinderella AND had the lead in that Diana Ross flick. ABC was very good to Brandy in 1999.

She sang "Have You Ever?" and had a costume change before going back to her hosting duties. She helmed Cinderella AND had the lead in that Diana Ross flick. ABC was very good to Brandy in 1999.

"Do you believe in life after love?"

I quote because this wasn't performed the way the other songs were performed. Oh, no. This was Cher. This was Cher in this career resurgence of 1999 and she performed this song through a story. Much like her music video, it involved a bunch of young kids, and colors and... something. I don't understand it but basically it's what Pink does now at every award show or what Madonna did during her VMA performances. It was all show and it was all good.

I quote because this wasn't performed the way the other songs were performed. Oh, no. This was Cher. This was Cher in this career resurgence of 1999 and she performed this song through a story. Much like her music video, it involved a bunch of young kids, and colors and... something. I don't understand it but basically it's what Pink does now at every award show or what Madonna did during her VMA performances. It was all show and it was all good.

MORE '90S CANADIANS!

The Wilkinsons. Look them up. They rocked.

Of course the Dixie Chicks won.

But look at their outfits. SO '90S. FLORAL, HOT PINK, METALLIC.

But look at their outfits. SO '90S. FLORAL, HOT PINK, METALLIC.

Elvis Costello and Burt Bacharach performed.

Did they hit their stride in the '90s? I can't recall.

Did they hit their stride in the '90s? I can't recall.

D.L. Hughley had a new show.

The woman on the right? Yeah, tube tops and wearing them like that were a thing. They were so much a thing, it was totally cool to wear them on television like that.

The woman on the right? Yeah, tube tops and wearing them like that were a thing. They were so much a thing, it was totally cool to wear them on television like that.

Enrique Iglesias.

Oh, I'm just saying Enrique Iglesias still remains hot. He's hot in the '90s and he's hot now.

Oh, I'm just saying Enrique Iglesias still remains hot. He's hot in the '90s and he's hot now.

Trisha Yearwood and Garth Brooks performed together.

I don't think they were together then? But they sang a song about being in love with each other. When I was a kid, I thought they WERE married. I was wrong. It didn't happen until later.

I don't think they were together then? But they sang a song about being in love with each other. When I was a kid, I thought they WERE married. I was wrong. It didn't happen until later.

Aerosmith won and didn't show up.

They had "I Don't Wanna Miss A Thing" which was one of the biggest songs ever and they had a great reign there in the late '90s. Shawn Mullins also made that face here.

They had "I Don't Wanna Miss A Thing" which was one of the biggest songs ever and they had a great reign there in the late '90s. Shawn Mullins also made that face here.

Donnie and Marie were there!

Did they do things in the '90s? Can't remember. They had a talk show in 2000. But they told us who were the top concerts in 1998. They devoted time to telling us that on television. Did I mention this show ran three hours long?

Did they do things in the '90s? Can't remember. They had a talk show in 2000. But they told us who were the top concerts in 1998. They devoted time to telling us that on television. Did I mention this show ran three hours long?

Chaka Khan was there to present.

She read the best alternative artist? Wha? The winners were Pearl Jam and they were up against Green Day and Third Eye Blind. Those are three '90s powerhouses of alternative music right there.

She read the best alternative artist? Wha? The winners were Pearl Jam and they were up against Green Day and Third Eye Blind. Those are three '90s powerhouses of alternative music right there.

Goo Goo Dolls, provider of epic '90s songs, were there.

They sang "Slide" which is one of my favorite songs of all time. The '90s were awfully good to the Goos.

They sang "Slide" which is one of my favorite songs of all time. The '90s were awfully good to the Goos.

People didn't need to be too cool or put together in the '90s.

Today? This would've made NATIONAL NEWS about Brandy and Melissa Joan Hart not taking their jobs seriously! Then? They were... having an awesome time.

Today? This would've made NATIONAL NEWS about Brandy and Melissa Joan Hart not taking their jobs seriously! Then? They were... having an awesome time.

MORE ANIMAL PRINT.

Enough said.

Enough said.

GARTH BROOKS WINS ALL THE AWARDS.

He is the Celine Dion of 1999 and every year before this one.

He is the Celine Dion of 1999 and every year before this one.

But let us not forget who the country queen was...

Shania was the Taylor Swift of the '90s. All of her country songs became crossover hits to where she was recording the pop version and the country version of her songs like, for example, "From This Moment." One was a duet with country star Bryan White and one was not.

Shania was the Taylor Swift of the '90s. All of her country songs became crossover hits to where she was recording the pop version and the country version of her songs like, for example, "From This Moment." One was a duet with country star Bryan White and one was not.

The Wayans and Daisy Fuentes.

This was like... the WB meets MTV.

This was like... the WB meets MTV.

Oh, look, more Will Smith.

But... soul? Mmm... I don't know about that one, AMAs.

But... soul? Mmm... I don't know about that one, AMAs.

Snoop and Bill.

I'm sure none of this was awkward.

I'm sure none of this was awkward.

'90s Janet was pretty huge.

She had a great run in the early '90s and left the '90s on top of her game and she was sweet enough to tape a video message. Aww.

She had a great run in the early '90s and left the '90s on top of her game and she was sweet enough to tape a video message. Aww.

'90s costume changes!

Melissa Joan Hart looks like she's going to Clarissa's prom. Na, na, na, na, na...

Melissa Joan Hart looks like she's going to Clarissa's prom. Na, na, na, na, na...

This wouldn't have been a '90s show WITHOUT Tia and Tamera.

You can't have the '90s without Sister, Sister. You just can't.

You can't have the '90s without Sister, Sister. You just can't.

Did you think she WOULDN'T win this year on the heels of Titanic? You were wrong.

My heart will go ooooooooooooooooooooon... I'll never let go, Celine.

My heart will go ooooooooooooooooooooon... I'll never let go, Celine.

Bye, '90s nostalgia fans! Bye!

And the show was over. Brandy was upset, too, but at least they had a great time and so did I!

And the show was over. Brandy was upset, too, but at least they had a great time and so did I!

All screencaps courtesy of my VHS and award show copyright belongs to ABC.

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