38. Grandpa Gene
Showcase Episode: "The Arrangements"
The father-in-law from hell, and Don Draper deserves no less. Betty's dad is a WWI vet who used to fine his kids for small talk. He puts salt on his ice cream, shows off his war medals to his grandson ("I should have another one for beating the clap") and constantly baits Don. The only person on earth he respects? Sally, the girl everybody else ignores. Grandpa Gene gives her driving lessons and makes her read The Decline and Fall of the Roman Empire out loud every night. He's the first adult to tell Sally she's smart. Let's hope she remembers him fondly, since nobody else will.