Here's a lesson in Simpsons chart history that would surely make Edna Krabappel proud.
Simpsons-related music first appeared on Billboard's charts shortly after the show's launch. On Jan. 26, 1991, The Simpsons Sing the Blues soared to No. 3 on the Billboard 200 albums chart (below Vanilla Ice's To the Extreme, at No. 1, and Madonna's The Immaculate Collection, at No. 2). In addition to original tracks, the album sports covers of songs by Chuck Berry and Billie Holiday, among others, sung by the show's characters.
Meanwhile, two of the set's original songs became chart hits. "Do the Bartman" danced to No. 11 on Hot 100 Airplay (subsequently replaced by Radio Songs as the Hot 100's airplay component chart) and "Deep, Deep Trouble" reached No. 69 on the Hot 100.
Notably, "Bartman" was not released as a commercially-available single on its own (on CD, cassette or vinyl, in a pre-download era) and, per rules in place at the time, was ineligible to hit the Hot 100. Still, the novelty song's airplay reflected the rapid ascent of The Simpsons and, specifically, Bart Simpson (voiced by Nancy Cartwright). Also fueling its success: rumors that it was written by Michael Jackson (who's name-checked in it). To date, Simpsons creator Matt Groening has stated that Jackson, an early fan of the show, co-wrote "Bartman" with friend Bryan Loren; in 2015, Loren asserted that he wrote the song himself (although noted that Jackson provided the song's title).
As for "Trouble," it boasts its own high-profile credits: it was written and produced by Groening and DJ Jazzy Jeff.
Six years later, The Simpsons took a note from Stevie Wonder's handbook with Songs in the Key of Springfield, a 39-track soundtrack of original tunes from the series. The set reached No. 103 on the Billboard 200 chart dated April 19, 1997 (coincidentally, the 10th anniversary of the Simpson family's first Tracey Ullman Show appearance).
Following the non-charting (d'oh!) studio LP The Yellow Album 1998, Go Simpsonic With The Simpsons, a 53-song soundtrack of songs from the show, dented the Billboard 200 with a No. 197 peak on Nov. 20, 1999. Guests on the release range from alt vets Sonic Youth and The Ramones to country's Hank Williams Jr.
In 2007, the Hans Zimmer-produced soundtrack to the long-in-the-works The Simpsons Movie reached No. 108 on the Billboard 200, as well as No. 8 on the Soundtracks chart. It includes a cover of The Simpsons' theme song performed by Green Day, which reached No. 54 on Digital Song Sales (and No. 6 on the Hot 100's Bubbling Under chart).
And, while we're on the subject of musical Simpsons, 13 titles by actual artists with the surname Simpson have hit the Hot 100's top 40. Seven belong to Jessica Simpson; four to her sister, Ashlee; and two to Valerie Simpson of husband-and-wife R&B duo (Nickolas) Ashford & Simpson.
Jessica has charted the highest-peaking Hot 100 hit by a (non-animated) Simpson, as "I Wanna Love You Forever" climbed to No. 3 in 1999. In second place? Ashlee, with 2004's No. 5-peaking "Pieces of Me" (not to fan the flames of a Bart vs. Lisa-like sibling rivalry).