The Simpsons has long hinted at the sexual orientation of Waylon Smithers. True, the show has never outright said he’s gay, but everyone seems to know it’s true.
Except for Mr. Burns.
Our story opens with Burns and Smithers going skydiving. Heck, the plane is flying over the show’s cloud-based title (nice gag there), and Burns jumps but loses consciousness and falls out of parachute. It falls to Smithers to dive down, grab Burns, and bring his boss safely to the ground. Smithers does so with a rainbow-colored parachute with Burns’ face on it.
Having brushed by death, Waylon wants to tell Burns he’s in love with the old man. Burns cuts him off at “in love with” by finishing “with your own voice,” so a dejected Smithers goes to work and takes his misery out on Homer, Lenny, and Carl. The guys meet up at Moe’s later with the plan to find Smithers a woman…who can then find Smithers a man.
See, the show basically said it’s common knowledge that Smithers is gay, and it’s no big deal. That sounds about right.
Taking a tip from Marge, Homer goes on Grindr, an app Marge found when looking for a pepper grinder. Heck, Homer finds his identical copy there, but being unable to pick among the many gay men of Springfield plus guest star George Takei, the Simpsons just invite all the guys over for a party and then get Smithers to show up. And that works, though Smithers sees right through the ploy, when Smithers meets Julio tending bar and the two hit it off, so much so that Burns is left to actually do things for himself.
And then Smithers, happier than he’s ever been, quits his job. Burns goes looking for replacement Smithers like Lindsay Naegle, but they tend to be a lot more…moral than Burns likes.
But things don’t work out for Smithers. He’s still thinking about Burns. Even when he and Julio go to Julio’s Cuban homeland, a place Smithers has been to before, he can’t stop thinking about Burns. Meanwhile, Burns knows he needs Smithers back.
That leads to a dinner reconciliation, where Smithers doesn’t want money or a letter of apology written by Burns’ attorneys, he just wants a sign Burns cares. And the old man does by giving his longtime toady a performance review of “Excellent!”
Oh, and for some reason Springfield Elementary is doing a school play of Casablanca. Really? Lisa gets cast as Ilsa, so Milhouse auditions for Rick. He’s the only one until some Humphrey Bogart kid named Jack shows up and wows Skinner. Milhouse is in the dumps until Bart advises him, as Jack’s understudy, to take care of Jack. That means hiring the bullies to beat Jack up, but Jack beats them up, but using the merry-go-round to pound Dolph, Jimbo, and Kearney just gets him suspended by Skinner. But then we learn Milhouse is a terrible actor, but Marge has advice for Lisa in that praising and showing support for an incompetent man can fix things. To prove it, she praises Homer for finishing the tax return, and Homer fixes a major math mistake on the spot.
Say, Marge and Homer know how to play each other very well.
As it is, Milhouse gets the praise and he’s great on opening night. Then we learn it was really Jack in a Milhouse disguise.
That kid is better than we thought.
But they were doing Casablanca?!?