THANK YOU, ANON. I THOUGHT NO ONE WAS GOING TO ASK.
This is no particular order. Also, there are more than five. But really, you can’t make choose between favorites.
Butch Guice:
The panel below is from World Walk Hulk. I really love the musculature, it’s consistent for someone of his stature & physicality. If we take ‘dark’ to mean sad, brooding, & depressive then Tony is definitely tall, dark, & handsome.
Iron Man: Director of S.H.I.E.L.D. #20 (2007)
Adi Granov:
If I had to pick a favorite, it’s this. This is from the first issue of the Extremis arc. It’s the comic I read when I want to remember why I love comics & why I love Tony.
Iron Man #1 (2004)
Alex Maleev:
I love that Tony here doesn’t look like the hyper masculine ideal. He’s not a super soldier, after all. He’s just a man in a can. A very, very good looking man. But still a man…with a weak spot for spies.
International Iron Man #3 (2016)
Leinil Franics Yu:
My second favorite Tony. Yu blessed us with his silver fox President Stark in Secret Wars: Civil War but this panel is just too good. Peak Stevetony angst.
Avengers #29 (2014)
Here are some honorable mentions:
Chris Samnee:
I love his style. Absolutely loved this take on Black Widow & her complicated past with Tony.
Black Widow #6 (2016)
Phil Noto:
Black Widow #12 (2014)
Valerio Schiti:
He’s working on Tony Stark: Iron Man. The cover, which was released a few days ago, is absolutely beautiful.