Hearing distant music one night, Lisa sneaks out of her room to follow it. She finds a saxophone player, Bleeding Gums Murphy, playing some blues. Murphy teaches Lisa how to express her sadness on the sax and plays with her until Marge finds her and exclaims, "Lisa! Get away from that Jazz Man!". The next morning, Marge drops off Lisa at school and tells her to smile no matter how she feels. She sees Lisa hiding her true feelings and classmates taking advantage of her and becomes mad. Just then, Mr. Largo comes out and denies Lisa her creativity. Realizing that that is reason why Lisa is sad, Marge becomes furious, floors the pedal, takes Lisa back, and drives away in an instant. Marge tells Lisa that it is best to be herself and if she does feel unhappy about life, Lisa can talk to Marge about it. When Lisa hears this, she feels happy again.
Meanwhile, Homer takes lessons from a local video game wizard named the Champ for a rematch with Bart. Just as he starts to win against Bart, Marge unplugs the TV to announce Lisa's recovery. Seizing the opportunity to maintain his undefeated status as boxing champ, Bart gleefully announces retirement from the ring, to Homer's disappointment. Afterwards, the Simpsons visit a jazz club to hear Bleeding Gums Murphy sing a number written by Lisa.
Mr. Largo, Lisa's music teacher, was partly inspired by a music teacher Matt Groening had as a kid. The designs of the boxers in the video game Homer and Bart play were loosely based on Homer and Bart, and the referee in the game was based on a character from Matt Groening's Life In Hell comic strip. Bleeding Gums Murphy was loosely based on the famous blues musician Blind Lemon Jefferson.
Ralph Wiggum, Bleeding Gums Murphy, and Jacqueline Bouvier (during Marge's childhood flashback) makes their first appearances on The Simpsons in this episode.
The authors of the book I Can't Believe It's a Bigger and Better Updated Unofficial Simpsons Guide, Warren Martyn and Adrian Wood, said: "Certain scenes of this, the most syrupy of Simpsons episodes, sent viewers raised on the later seasons scurrying to the bathroom. Yes, the final moments may give you goosepimples, and are a world away from the anti-schmaltz normally associated with the series, but there is still much to recommend here. In fact, the Homer-Bart subplot is more successful than the main storyline; Homer's nightmare about their relationship is genuinely disturbing." In a DVD review of the first season, David B. Grelck gave the episode a rating of 2.5/5 and adds "Lisa develops much of her future personality in this episode. The family dynamic is starting to fall into place, as is the relationship between Homer and Lisa.