I failed to get back behind (earlier) than my wife's family's oldest photo in this post, but I did this afternoon over lunch!
I was just perusing my tree on ancestry.com to see where things were in various ancestral branches and came across this one:
This is my 7GRGR, Magdeleine St Laurent. She married Jean-Baptiste Brouillard. She was born in 1700, he in 1690. Magdeleine died in 1736, making this photo which, if authentic, would put it nearly 30 years before the aforementioned Rebecca Machado photograph on my wife's side!
Her connection to me is as follows:
Magdeleine St-Laurent (1700 - 1736)
is your 7th great grandmother
Son of Magdeleine
Son of Jacques-Julien
Daughter of Francois Xavier
Daughter of Marguerite
Son of Christine
Son of Edward "Henry"
Daughter of (Henry) Clayton
Son of Jennie Delphine
You are the son of Ronald Lloyd