Hey! I came in here to mention HBC, but I think she’s really from a dystopian/re-boot future. The threads she wears to some red carpet events are sometimes … interesting. Definitely not from the past or present.
Maria De Medeiros always make me think of a Flapper.
He’s not a celebrity, per se, but ABC newscaster David Muir looks like he’d fit right in with the cast of Mad Men, or any other genuine 1950s-1960s-era set piece.
That was supposed to be a satire of Gabby Hayes.
James Carville is from the year 3000, after humans have begun interbreeding with aliens.
Does’t help me place this person. Although I do agree that there is a resemblance to the person in the lower front of the Civil War photo.
Roddy
Postcards Johnson is right.
Maggie Gyllenhaallooks like she stepped out of a silent film, or perhaps the Great Depression, to the point where she looks out of place in modern styles.
Nemo Johnson is right about Postcards Johnson being right!
Tilda is a good pick.
I think Gretchen Moll could have stepped out of the 20’s. Even her name seems to fit.
what i can’t understand is why johnny depp and helena bonham carter never hit it off. they could spend the rest of their lives wearing garish make-up and costumes in fashion before the great war.
as an aside, which present-day actress do you think looks best in a 30s charslton outfit drinking champagne with confetti showering her, and dancing all night with tuxedos?
Oh wow, I never thought of that, but you’re dead on.
Another flapper wannabe is Evan Rachel Wood. I don’t know how successful at it she is, or whether she picked it up trying to emulate her rival-at-the-time Dita Von Teese, but there ya go.
Rachel Weisz. The perfect best friend for the 40’s and 50’s blonde star.
Aaron Paul is in the show Breaking Bad, if that helps.
Well, she’s hooked up with Tim Burton which is even better! 
In her heyday, Bernadette Peters has always been a World War II pin-up girl.
~VOW
I was watching Suburgatory last night, and the actress who plays the daughter Tess (Jane Levy) http://www.google.com/imgres?q=Jane+Levy&hl=en&sa=X&rls=com.microsoft:en-us&tbm=isch&prmd=imvnso&tbnid=4mIPVz83SVKaUM:&imgrefurl=http://hollywoodyoungblood.us/category/jane-levy/&docid=h6YXzw47gYUe1M&imgurl=http://hollywoodyoungblood.us/wp-content/uploads/2011/10/100911_JaneLevy_005.jpg&w=814&h=1000&ei=PFu8TpzWGMTu0gGU8onLBA&zoom=1&iact=hc&vpx=983&vpy=109&dur=1203&hovh=249&hovw=202&tx=80&ty=145&sig=109049584213337069738&page=1&tbnh=115&tbnw=111&start=0&ndsp=25&ved=1t:429,r:23,s:0&biw=1280&bih=572 reminds me of a young Maureen O’Hara.
So does Tim Blake Nelson, which (along with his voice) is why he was so perfect for Oh Brother Where Art Thou. In fact he looks so much like that it’s hard to believe him when he plays a modern day cop or a businessman or whatever.
Charles Durning would have fit in perfect in the late 19th century when “Fat=Prosperous”, which is why he always works perfectly when playing a figure from that era or a throwback figure like a corrupt political boss (which he’s played several of in his career).
Burt Reynolds will never not look like he’s from the 1970s.
IMDb FFS.