18 Years Ago Today: Britney on Letterman

[DoYouDare?]

18 years ago today, Britney made a surprise appearance on the Late Show with David Letterman. She wore a belted black romper, paired with peep toe slingback pumps, & her hair was styled in a blonde bob with bangs.

However, her time on the show was akin to a cameo (skit), as she made a sudden entrance from behind Letterman’s desk, only to express that she was looking for Will Ferrell, & simply walking off once she was directed to her destination by the tv host himself.

Surely, the audience was ecstatic to see her back on television following her first hiatus, & even though she didn’t reveal much about anything, it was certainly an exciting moment.

Here’s the clip:

To think she was already recording Blackout during this time, & filed for divorce just a day after this appearance, makes it feel that much more iconic, in my opinion.

Do you remember this moment?

[AquaSpears]

I didn't even know that happened

must have been so random but this is fun

[LizeS_]

I was a sophomore in high school 😩 I remember everyone was schoked, we were all thinking a big comeback was in the cards lol little did we know...it's crazy to think it's been 18 years! 

[Hype Boy]

That appearance was solely to create buzz. That same day, she filed for divorce from Kevin, and by the next day, she was on the front page of every media outlet for that reason. Larry re-entered her life (who was fired) briefly during this period, then he introduced Britney to Paris, and the rest is history.

 

Edited November 6 by Hype Boy

[thesimplelife]

 

[Fita]

Lol

[whenthedogscaneout]

That was a great look. Her divorce seemed so promising, Rosie celebrating it too with confetti… in retrospect that’s all so weird. She was going through a divorce and had to make it seem fun and exciting. 

[eduardo1993]

The calm before the storm... I miss that time

[DollyParton]

Gosh, this was such an amazing time. Literally EVERYONE was rooting for her after a long period of a lot of media negativity towards her. She almost got an standing ovation when she showed up at some award show to present an award…Sadly it lasted very short, cause it took only a month before Paris Hilton got into the picture 

Edited November 6 by DollyParton

[thesimplelife]

19 minutes ago, DollyParton said:

Gosh, this was such an amazing time. Literally EVERYONE was rooting for her after a long period of a lot of media negativity towards her. She almost got an standing ovation when she showed up at some award show to present an award…Sadly it lasted very short, cause it took only a month before Paris Hilton got into the picture 

even TMZ was by her side. it’s just crazy how everything changed so fast. 

[Crazy4BRITNEY3.3]

I remember it as if it was yesterday... Everyone was so excited about her being back in great shape, the new haircut, newly-single, fun and cool as she used to be pre-k-fed... Ahh the future seemed so bright 💗

[CJMCH]

13 hours ago, DoYouDare? said:

18 years ago today, Britney made a surprise appearance on the Late Show with David Letterman. She wore a belted black romper, paired with peep toe slingback pumps, & her hair was styled in a blonde bob with bangs.

However, her time on the show was akin to a cameo (skit), as she made a sudden entrance from behind Letterman’s desk, only to express that she was looking for Will Ferrell, & simply walking off once she was directed to her destination by the tv host himself.

Surely, the audience was ecstatic to see her back on television following her first hiatus, & even though she didn’t reveal much about anything, it was certainly an exciting moment.

Here’s the clip:

To think she was already recording Blackout during this time, & filed for divorce just a day after this appearance, makes it feel that much more iconic, in my opinion.

Do you remember this moment?

Larry was all in for the divorce PR, putting her on a new look, looking happy, hot and healthy. This was the same day where she met Bloodshy & Avant to record freakshow. His huge mistake was presenting her to Paris Hilton.

Seems like the widescreen file was lost... until now!

 

Edited November 6 by CJMCH

[PrinceAli89]

57 minutes ago, CJMCH said:

Larry was all in for the divorce PR, putting her on a new look, looking happy, hot and healthy. This was the same day where she met Bloodshy & Avant to record freakshow. His huge mistake was presenting her to Paris Hilton.

Seems like the widescreen file was lost... until now!

 

Thank you so much for sharing this in this amazing quality.

Good times!  

[DoYouDare?]

1 hour ago, CJMCH said:

Larry was all in for the divorce PR, putting her on a new look, looking happy, hot and healthy. This was the same day where she met Bloodshy & Avant to record freakshow. His huge mistake was presenting her to Paris Hilton.

Seems like the widescreen file was lost... until now!

 

I agree, & you did a wonderful job restoring the video, I’ve already given it a thumbs up on your YT channel.

I was wondering about the Bloodshy & Avant studio sessions, because I felt so certain she was wearing the same outfit, & she was:

[Style.]

I didn’t like this look, it made her appear more mature. She was completely mismanaged; they didn’t know how to market the biggest brand on the market at that time.

Edited November 6 by Style.

[DoYouDare?]

11 hours ago, Hype Boy said:

That appearance was solely to create buzz. That same day, she filed for divorce from Kevin, and by the next day, she was on the front page of every media outlet for that reason. Larry re-entered her life (who was fired) briefly during this period, then he introduced Britney to Paris, and the rest is history.

 

You’re right, I remember she was everywhere. However, she filed for divorce on Nov. 7th, a day after her Letterman show appearance.

[DoYouDare?]

3 hours ago, Style. said:

I didn’t like this look, it made her appear more mature. She was completely mismanaged; they didn’t know how to market the biggest brand on the market at that time.

On the contrary, I think she was well managed during the time of this video. Plus, 2006 was a different era, & 25 yr olds were seen as “too grown” to dress a certain way, but if she would've been 25 right now, they’d probably style her in more edgy/vibrant looks, like Dua Lipa, or Sabrina Carpenter, Taylor Swift, etc…

She still looked stunning, in my opinion.