Madonna

LOOK AT THIS LITTLE PICTURE. Given how instrumental to her image a white dress look became, this is a hoot. It's her First Communion and IT IS ADORABLE.

This was tagged as her high-school yearbook photo.

This is ALSO supposedly in her yearbook. Even icons start out as just regular ol' people.

Another one supposedly from the yearbook. It's hilarious and dramatic. God, I love yearbooks.

Fall 1978

This is from a series that is all about how she moved to New York to study dance.

1979

Ditto, from the following year. I have never thought this before, but in this photo Madonna looks like a young Joan Collins.

1979

Look at Serious Ballet Madonna! So DETERMINED.

1979

And this was her headshot. Her eyes... they're really majestic. It's also so interesting to me how straightforward these shots are --like, who knows when MADONNA started percolating in the head of Madonna Louise Ciccone. Shortly after this, she ended up forming a band with her boyfriend called Emmy and the Emmys. I'd say she upgraded.

Madonna in 1983

Naturally, things took a turn for the wacky.

Madonna, 1984

This basic take on Madonna was my Halloween costume for YEARS as a kid. All the bracelets! I added fingerless mesh gloves, from a later era, but the vibe was this.

I think back on all those incredible pop songs, and they are SO specific to an era and so perfect for what she brought to the table. And she was so unique. Would she rock the world as much if she launched in 2023?

Madonna 1984

And then she made it through the wilderness. Somehow, she made it through.

Madonna 1985

She certainly stuck to an aesthetic.

Desperately Seeking Susan - 1985

This movie was the height of cool to me. The giant earring! THE JACKET. I was Rosanna Arquette, wishing I could be Madonna.

Desperately Seeking Susan - 1985

THE RAY BANS. How I wanted some.

Madonna 1985

As usual, that is a lot of look.

Huey Lewis and Madonna

That's not the BEST hairpiece on Madonna here. But I do enjoy that TWO icons of pop are in the same photo.

George Harrison and Madonna, 1986

Somehow, I did not know that George Harrison produced Shanghai Surprise, a stinker of a movie that MIGHT be where Madonna and Sean Penn met? They were married by the time it came out and started dating the previous year, so that might line up. Its IMDb reviews are, "It's actually much worse than you've heard," and, "It stinks so bad, I can't think," and, of course, "Nice tie, shame about the film." I may need to watch it immediately.

Shanghai Surprise - 1986

This relationship was a disaster, but they looked sharp.

1986

I didn't remember that Madonna had gone brunette real quick in this period, but I guess she did? Unless they mis-dated this. It feels a tad more like the "Like a Prayer" era.

Who's That Girl? - 1987

Who could forget THIS haircut.

1988

We then quickly moved onto the Papa Don't Preach era. A CLASSIC use of a Breton stripe.

Madonna

This photo is undated, but I assume it's from around this time? All I know is, somewhere in Minnesota, a young man named Brandon Walsh took this photo to his hairdresser and said, "I want this."

Madonna in the Video for " Like a Prayer " - 1989

ICONIC. The song, the video, all of it.

Madonna 1989

THIS is where you're like, "Ohhh, Madonna really WAS on Gwen Stefani's childhood mood boards."

Apr 1990

And then: BLONDE AMBITION. The tour I wish I'd been old enough to go see. Or, well, I was old enough, but I hadn't discovered concerts yet, and I don't think my parents would have let me go (also would NOT have gone with me).

Ditto, honestly. This photo is ALSO undated so I just sort of guessed it might fit in around here because that's when it showed up in the search. Sometimes those get messed up, though.

Madonna 1991

Here, she's at Cannes for her movie "In Bed With Madonna," dressed in Playtex's finest.

A League of Their Own, 1992

All the way, Mae!

With Luke Perry

Undated, so I'm guessing again. I couldn't NOT include Madonna and Dylan McKay chilling out.

Madonna 1992

And then: full nipple.

1993

Here she looks like Lori Petty to me.

Sep 1993

This is her "Girlie Show" tour. What a costume. That's stunning.

1994

Here, she's at the Jean Paul Gaultier Ready to Wear Spring/Summer 1995 show in Paris. I'm not sure why the dog is involved, and neither is the dog.

1995

Again, you can't tell me Gwen Stefani didn't love this woman.

Evita - 1996

I can't leave out Evita.

1999

We covered the Evita premiere in detail during the pandemic. This is very festive.

1998 Fire and Ice Ball

I JUST noticed her nipple staring at me through a peephole.

1998 Golden Globe Awards

I would argue that none of this is her best.

1999 Grammys

For a weird second I thought she was wearing dramatic shoes, but no, she just won a bunch of awards. Those SHOULDERS. I'm gonna drop and do 20.

2000

And now we enter the MADGE era, when she married Guy Ritchie and turned British for a second.

2001

I did NOT remember that Madonna and Guy Richie did a whole "exiting the Christening" photo op with Rocco. And in a VEIL, no less.

2002

I know we don't cover the royals, but I could not pass up this photo of whatever Madge's face is doing.

2005

Ah, the genie pants and leotard. What a combo.

2008

That could be worse!

2009

Here, she's at the Met Gala for the "Model as Muse" theme. Wearing some kind of hybrid between a scarf and a scrunchie.

2011

This is the Cannes premiere of her movie about Wallis Simpson, and honestly? She looks fanfreakingtastic.

2013 in Givenchy

This is the Punk themed Met Gala, which, sure. Although I kind of wish she'd gone as herself from the 80s; THAT feels like a punk move.

2014 Grammys

She showed up at this event in matching outfits with her son David. This is, I think, the part of her life where I get on the rollercoaster of thinking she's being groovy...

2015

... and thinking she's trying really hard to be a certain flavor of cool that could stand to evolve.

2015 in Moschino

This was "China: Through the Looking Glass," and it's a custom gown promoting one of her albums. Which is both AMAZINGLY egotistical and not REMOTELY on-point.

2016 in Givenchy

I wish this one hadn't happened. (It was for Manus x Machina, which was admittedly a theme a lot of people didn't gel with, but that's not even the issue. It's just... too much.)

2017 in Moschino

This was the Rei Kawakubo theme. I'm not sure she or Jeremy Scott really cared that much. It's... fine?

2018

Well, you knew Madonna would go big for "Heavenly Bodies: Fashion and the Catholic Imagination."

2018 in Temperley London

I have a whole lot of questions about decisions she made here.

2021

I do not think Covid was kind to Madonna's overall well being. If I recall correctly, that's when her Instagram took a weird turn. I know this is Madonna we're talking about, but this is A LOT.

2021

It went down from there.

2023 in Mugler

I just hope so profoundly that she's healthy and solid, and puts on a show that makes her very proud.

Happy 65th Birthday, Madonna: A Retrospective

I meant to put this up on Madonna's actual birthday, which was Wednesday, but I didn't get my act together in time. So now it's more of a birthday WEEK post. The Queen of Pop had to postpone her new tour because of that scary health issue, but she's now scheduled to debut in Europe in October and then swing through North America, so I assume she's recovered?!? Since seeing her at the Eurovision final, I don't know if I could get excited about seeing Madonna in concert anymore -- I feel like I missed the window for it to be a Bucket List experience -- so it's fun to look back and remember what a revelation she was, and what an icon she will always be. [Photos: Moviestore, MediaPunch, Rebel Images, Crollalanza, Unimedia, ANL, Eugene Adebari, Bei, Dave Lewis, Charbonneau, Alan Davidson, Masatoshi Okauchi, David Fisher, Matt Baron, Erik Pendzich, Jim Smeal, Broadimage, Rob Latour/Shutterstock, Michael McDonnell/Archive Photos/Getty Images, Dave Hogan, Michael Putland/Getty Images, Herb Ritts/Orion/Kobal/Shutterstock, Ron Galella/Ron Galella Collection via Getty Images, Aidan Sullivan/Mail On Sunday/Shutterstock, Handmade/Mgm/Kobal/Shutterstock, Oscar White/Corbis/VCG via Getty Images, Steve Allen / Liaison Agency,Cardinale/Sygma via Getty Images, Cinergi/Kobal/Shutterstock, Henry Lamb/Photowire/BEI/Shutterstock, Diggzy/Jesal/Shutterstock]