Marge and Lisa visit the nail salon where they engage in a spirited debate as to whether a woman can be smart, powerful and beautiful all at the same time and spin four tales of famous women featuring famous Springfield faces: Selma as Queen Elizabeth I, Lisa as Snow White, Marge as Lady Macbeth and Maggie as Howard Roark, the idealistic architect protagonist from Ayn Rand’s The Fountainhead.

Lisa invests in Nelson's brand-new business venture, but soon realizes that her friend's instant success might lure him away from the classroom. Worried that his judgment might be clouded, Lisa introduces Nelson to the well-educated and successful creator of Facebook, Mark Zuckerberg, only to find out that he too dropped out of school.

Moe is flying high after venture capitalists take a shine to his homemade whiskey, while Grampa, after injuring himself babysitting Bart, decides he'd rather be looked after by his grandson than be at the nursing home. Also, Lisa voices her displeasure at a hologram of music legend Bleeding Gums Murphy, and Sonny Rollins (as himself) shows up to ask her to stop all that jazz about boycotting a record label.

Lisa brings in assembly woman Maxine Lombard to put a stop to Mr. Burns' fracking operation, but is taken aback when the two political opponents find themselves attracted to one another.