After winning the chance for his photo to appear on a Duff beer calendar, but losing out when the calendar appears with stickers covering his face, Moe gets a facelift. The resulting surgery makes him handsome and then Moe takes revenge on those who wronged him because of his looks in the past, including the producer of a soap opera. Of course his new looks get him the part, until he and Homer become privy to some plot lines that threaten to write him out of the show. In anticipation, they decide to go out "in a blaze of sour grapes".
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One morning the fire alarm goes off, everyone grabs something of theirs and rushes to the car, unfortunately Homer set off the fire alarm to get them to the beer convention. As it turns out Moe is competing in a bartender competition. Unfortunately Moe does have some tight competition from Michael Finn, a hunky, Irish bartender; and Titania, a large-chested female bartender who's slated as the audience favorite, but he comes through in the end when Titania disqualifies herself for not tossing her drunk and Moe beats Michael in the drunk toss by going after Barney with a wooden plank with a nail in it. After winning the bartending contest, Moe is shunned by the Duff brewing company when his picture on their calendar has stickers over his face. After peeling away all the stickers, Moe is shocked to see how ugly he is (especially when Carl compares Moe's ugliness to Lenny's stupidity, Barney's drunkenness and Homer's laziness, baldness and weight). Moe become upset and he, along with Homer, Lenny and Barney began to cry while Carl Broke the fourth wall saying "See, this is why I don't talk much".
Moe gets a facelift, becoming very handsome, and sets out to do all the things he never could, including almost getting a date from a girl he liked in high school. He then tries out for a role on Soap Opera It Never Ends, who had turned him down years ago for being 'ugly-ugly'. Now with his leading man looks, he is offered the role of leading man Dr. Tad Winslow. The new episodes of Moe premiere and while Lisa is unsure if she'll accept Moe as Dr. Winslow, Marge doesn't mind as long as the show retains its regular points. In the episode Moe is in love with Cleo a mummy who was brought back to life. Moe's popularity is so incredible that ladies are soon hanging out in the bar which surprises the bar flies, and being surrounded by beautiful women (and Selma).
After misinterpreting a plot line, Moe thinks his character is being killed off. He sneaks Homer on to the set to make a guest appearance as an angel from the future, and gives away a year of the soap's story lines. The irate producer comes in and explains that Tad Winslow was only going to be killed off in a dream sequence. The producers go to fire Moe, but Moe quits, citing that he can get on any soap opera he wants because of his handsome face. Unfortunately, as he leaves, the set falls on top of him, turning his once-handsome face back to his original ugly mug.
Moe then returns to his old job at Moe's, which almost was going to be sold and turned into a Hooters, much to Homer's shock. Moe then wonders to himself why the set falling on his head turned his handsome face back to his old face instead of making a third, uglier face, but the episode gets cut off before he can continue the pondering.
In a short subplot, Maggie gets a pink elephant balloon from the Duff Days festival. Bart and Lisa see how happy Maggie is playing with it, then fight over who gets to play with it next. The balloon flies up the chimney and out of the house. Bart and Lisa chase after the balloon until it reaches an office building (and don't notice that Snake Jailbird just used Lisa's bicycle to simultaneously teach his kid how to ride and steal a bike) and ends up in the boardroom of a group of homosexual male Republicans looking for a symbol that says they're gay and Republican (when the balloon flies into their office, one of them comments that a pink elephant is "a little on-the-nose"). Bart and Lisa get the balloon back and one of the gay Republican members gives them a bumper sticker for a gay President running in 2084, which, according to the other members, is a realistic goal.