Moaning Lisa
Lisa wakes up one morning saddened. At school, she gets in trouble with her music teacher for improvising, and her gym teacher sends home a note to her parents saying she was reluctant to play dodgeball. At home, Homer and Bart pummel each other at video boxing, but despite Homer's attempts, he is unable to defeat Bart. Homer and Marge try to cheer Lisa up, but she is consumed with worry over all the suffering in the world. In her room, Lisa hears music coming from outside her window. She follows the music through town and meets Bleeding Gums Murphy, a soulful saxophonist playing the blues. Lisa learns about expressing herself through her music from him, only to be discovered and whisked away by Marge.

Homer goes to the arcade and enlists the help of a local video game wizard, while Marge takes Lisa to band practice. She tells Lisa to smile no matter how she feels inside, to suppress her emotions in order to be popular, and that happiness will follow. But when she sees Lisa hiding her true feelings and being taken advantage of by her classmates, Marge changes her tune and tells Lisa to be herself and her support helps Lisa to feel genuinely happy. When Homer returns home, he is about to defeat Bart in a rematch but Marge unplugs the game console to announce Lisa's recovery, while Bart declares his retirement as undefeated video boxing champ. Later, the Simpsons visit a jazz club to hear Bleeding Gums Murphy sing a blues number written by Lisa.

Marge Be Not Proud
Christmas is approaching, and Bart wants nothing more than the new, must-have video game Bonestorm. However, Marge refuses to buy it, due to the violence and potential distraction from Bart's schoolwork. Discouraged, Bart visits the local Try-N-Save discount store where Jimbo Jones and Nelson Muntz convince him to steal a copy of the game. On his way out of the store, Bart is caught by the store's strict security guard, Don Brodka, who tells Bart to leave and never return or risk spending "Christmas in juvenile hall".

Unaware of Bart's shoplifting, Marge takes the family to the same store to get their annual Christmas picture taken. Bart tries to avoid detection and trouble, but is spotted by Brodka, who shows a disbelieving Marge and Homer the security tape of Bart shoplifting. Disappointed by Bart's actions and concerned that she may be mothering him too much, Marge decides that he is old enough to make his own decisions and becomes distant with him. Bart is left out of family activities, such as decorating the Christmas tree and making snow statues, and he ends up spending time with Milhouse's mom for motherly comfort. Fearing he has lost Marge's love, he decides he must regain it.

Bart then returns home with a bulge in his coat. Marge confronts him, believing he was shoplifting again, and she finds Bart has hidden a picture of himself bought as a Christmas present for her. Marge is overjoyed, and in gratitude for receiving this early Christmas gift, gives Bart his—the new game that a store salesman told her "all the kids want", the golf simulator Lee Carvallo's Putting Challenge. Though profoundly underwhelmed, Bart looks into his mother's expectant face and thanks her.

someday i plan to steal a quarry

Classic.