From The True Blue video, directed by James Foley.
22 pictures ›

 

 

Between takes of the True Blue video.
2 pictures ›

 

 

In the True Blue video outfit at the 1986 MTV Awards.
2 pictures ›

 

 

Two versions of the 1986 Madonna.

 

 


From Who's That Girl, also directed by James Foley.
50 pictures ›

 

 


Making Who's That Girl.
23 pictures ›

 

 

Promotional shots for Who's That Girl with co-star Griffin Dunne.
23 pictures ›

 

 


Modelling an Martin Burguoyne jacket.
9 pictures ›

 

 

A leatherish True Blue Mads shot by Herb Ritts.
8 pictures ›

 

 

The cover session of the Look of Love single.
2 pictures ›

 

 


10 pictures ›

 

 

From the making of the Open Your Heart video.
6 pictures ›

 

 

Positive ID! Photo by Oscar White.
3 pictures ›

 

 

These two Herb Ritts pics are from the cover of the Live To Tell maxi single.
2 pictures ›

 

 

With Sean at an Amnesty International benefit.
5 pictures ›

 

 

With Sean at the premiere of At Close Range, the
film starring Sean that Madonna wrote Live to Tell for.
10 pictures ›

 

 


With Sean again.
16 pictures ›

 

 

Herb Ritts photo from the cover of Tatler Magazine, March 1986.

 

 

With Sean Penn and friends. The older guy is author Charles Bukowski.
5 pictures ›

 

 

Herb Ritts session.
5 pictures ›

 

 

Hailing a cab or something in New York.
2 pictures ›

 

 

From the video for Who's That Girl.
2 pictures ›

 

 

From Vanity Fair.
2 pictures ›

 

 

 

 

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