________ Never looked better than they did in _______

[I love Latina women]

Kerry Washington in Ray

 

[I love Latina women]

Madonna in dikk Tracey

 

[DaMos Supreme]

Kim Coles on In Living Color

I would go as far as the 1st season of Living Single.

 

[BXKingPin82]

Cameron Diaz in The Mask

This gotta be the only right answer.
Its like she aged like milk immediately after that film.

 

[DaMos Supreme]

Kerry Washington in Ray

I think she looked better in ‘I Think I Love My Wife’

 

[I love Latina women]

I think she looked better in ‘I Think I Love My Wife’

I forgot about that film

 

[ShaDynasty]

Sanaa in Love & Basketball. A lot of this is about age though.

An exception is Sandra Bullock, I think she was smashable in Gravity.

 

[Legal]

I think she looked better in ‘I Think I Love My Wife’

I'd be willing to consider "She Hate Me" too.

 

[I AM WARHOL]

Megan Fox in Transformers 1. 13 year old me was uncomfortable in the theater to say the least

 

[DaMos Supreme]

Sanaa in Love & Basketball. A lot of this is about age though.

This one is a bit challenging, because her appearances in ‘Disappearing Acts’ and ‘Brown Sugar’ may have something to say

 

[threattonature]

Rachel McAdams and Isla Fisher in Wedding Crashers. I thought both of them were sexy as hell in that shyt and that was back before I found white broads that attractive. But then I saw them in anything else and thought they were the most basic bytches ever.

 

[jadillac]

Sarah Jessica Parker in "Honeymoon in Vegas"

Yes, THAT Sarah Jessica Parker.

 

[SAINT]

Christina Milian in love don't cost a thing.

this.this.and this

 

[En Sabah Nur]

Kate Winslet in Titanic
Vivica Fox in Booty Call

 

[I AM WARHOL]

Jennifer love Hewitt in Heartbreakers