This song was probably from 2009 to 2014.
It was old school style.
The african american man (around 40+) was wearing a blue (I think) business suit and hat, he was holding a walking stick (I think, again :).
He was singing in front or inside a diner. I think there was a blue old cadillac or something and I think he was singing about a woman leaving him for someone with more money or him getting the girl because he had money… not sure.
I have had this song in my head for like 2 years now 🙁 Help!