Impossible

Tony’s parents died in a murder-suicide, not by the Winter Soldier. They faked that video to spare Tony so he wouldn’t know what Howard did.

I briefly had this thought in the movie- but even IF at the age his parents died he looked close enough to his 40 odd year old self to make the connection- first off- how many people does a normal person meet in 20 odd years? How many random encounters does a guy like Howard Stark have, and how much does he have on his mind that he would be like “oh.... you look like someone I briefly met decades before you were born one time for a couple minutes.... like what are the odds that would stick with him let alone he’d have the thought “maybe you’re a time traveler..” vs just thinking “these two people looked kinda similar...”