Smithers age confuses me. He was a baby when Homer was 13 in the "Blunder Years" and was also a nerd when Homer was in high school. How could he be in high school with Homer if Homer is 12+ years older than him? I've read Waylon is about 40-50, that means he is older than Homer. In "Walking Big and Tall", Waylon Smithers, Sr. was shown alive 30 years ago. In "To Cur With Love" Waylon Smithers, Sr. was also alive 28 years ago. He died when Smithers, Jr. was about 1, so that means Smithers is in his 20s. What age do you think Smithers is?