While staying in New York during a particularly hot summer, Miles typically had his apartment window open, and frequently heard teenagers blasting Hip-Hop, particularly the music of Def Jam Recordings, out of their boomboxes, but none of his music. Miles then decided he wanted to make an album that captured the sound of hip hop; though that decision isn't too surprising if you knew that one of his favorite albums at the time was Paul's Boutique. Calling up his friend and Def Jam owner/co-founder Russel "Rush" Simmons, Miles asked him to find some young hip-hop producers to help him create the sounds he wanted. Simmons proceeded to send Miles a stack of beat tapes from some of his best producers, including Chuck D and Flavor Flav, but the standout among them was a relatively-unknown producer by the name of Easy Mo Bee, who was also part of a group called "Rappin' Is Fundamental".
Davis and Mo Bee recorded and produced the majority of the album between January and February 1991, with Mo Bee and his R.I.F. bandmates providing their "doo-hop" sound to the album by contributing both rap and doo-wop influenced vocals, which inspired the album's eventual name of "Doo-Bop". Davis took a break from recording to tour and perform, including a performance at the 1991 Montreux Jazz Festival that would become Miles & Quincy: Live at Montreux, but died from a stroke later that year. At that point, only six tracks had been finished during the recording sessions, so Warner Bros. gave Mo Bee some of Miles' unreleased "RubberBand" recordings (which, according to Mo Bee himself, came from unreleased sessions Miles had with Prince) to make two more tracks "Miles would have loved" to finish the album.
Doo-Bop was released posthumously in 1992, and was mostly received negatively by critics, but nonetheless managed to win a Grammy for "Best Instrumental R&B Performance" in 1993; netting Miles his seventh and first posthumous Grammy. As for Mo Bee, he would continue to build his name by producing for future legends RZA and GZA, before breaking into the mainstream as the main producer of both The Notorious B.I.G.'s Ready to Die and Craig Mack's Project: Funk Da World in 1994. Davis would see one more posthumous album release with Rubberband in 2019, 27 years later.
- "Mystery" (3:56)
- "The Doo-Bop Song" (5:02)
- "Chocolate Chip" (4:41)
- "High Speed Chase"* (4:40)
- "Blow" (5:07)
- "Sonya" (5:32)
- "Fantasy"* (4:38)
- "Duke Booty" (4:56)
- "Mystery (Reprise)" (1:26)
* = Tracks that were made posthumously.
Just tropin' this Doo-Bop sound!
- Boastful Rap: And unlike most self-referential examples of this trope, the raps are centered around Miles and his trumpet skills.
- Genre Mashup: The album meshes jazz with rap, New Jack Swing and Doo-wop.
- Instrumental Hip Hop: Zigzagged - While the are pure instrumentals throughout the album, there's also three songs that contain vocals from Easy Mo Bee and his group Rappin' Is Fundamental.
- Jazz Rap: Miles was the first jazz artist to create a full-on hip-hop album, and Doo-Bop actually predated more ambitious jazz rap projects; like Guru's Jazzmatazz series, and the supergroup Buckshot LeFonque.
- Posthumous Collaboration: What Doo-Bop unfortunately became, since Miles died before the sessions could resume. "High Speed Chase" and "Fantasy" were the two tracks built from previously-unreleased recordings from Miles.
- Portmanteau: The album's title is derived from both "Doo-Hop" (Mo Bee's doowop/new jack fusion), and bebop.
- Sampling: Doo-Bop was the only time Miles himself sampled other peoples' music in his own. James Brown, Slick Rick, and even Gang Starr are among the artists sampled throughout the record.
- Special Guest: Easy Mo Bee's Rappin' Is Fundamental bandmates J.B. and A.B. Money show up on the title track, singing the hook and providing guest raps. Mo Bee himself is a subversion, as he produced the album with Miles.
- Spoken Word in Music: Miles himself can be heard speaking during "Blow" and "Duke Booty".
- A Wild Rapper Appears!: Because the album is largely instrumental, Mo Bee's verses serve as this.