45.
Waylon Smithers
The Simpsons
Voice: Harry Shearer
1990-present
Previous Rank: N/A
Our beloved Waylon Smithers is the neat, officious, and fanatically devoted personal assistant and adviser to Springfield’s legendary evil mastermind, C. Montgomery Burns, and he could not be happier about it. Every 104-year-old multi-billionaire needs someone to keep his nuclear power plant running, hop into his model airplane at gunpoint, and remind him when his heart stops beating again, and Smithers performs these duties admirably. He is the quintessential gay assistant, perfectly in control, willing to do anything no matter how demeaning, and criminally overlooked by his boss/obsession.
It has never been made explicitly clear whether Smithers is into all guys or just Mr. Burns, but he definitely loves his boss, which is good enough for us. Once he’s had the fantasy of Mr. Burns flying in through his bedroom window while he sleeps, there’s really no going back. But who can blame him? The greatness of Smithers is that he is the only one who understands how truly excellent Mr. Burns is and will work dawn to dusk to keep the villainy going. When we become eccentric billionaires, we can only hope we have someone as sycophantic as Smithers to lend a helping hand and assure us that the audience isn’t saying, “Boo!” It’s saying, “Boo-urns!”
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