2012–2014: GETCOMFORTable and ComfortZone

In December 2012, Saba shared his first project, GETCOMFORTable. The album is a "catalogue of young Chicago talents who join Saba in trying to make sense of themselves as rising adults in today’s world."^[5] The most popular song off of GETCOMFORTable was "Heaux" featuring well-known Chicago rapper, Mick Jenkins.

In 2013, Chance the Rapper and Saba joined forces on Chance the Rapper's album Acid Rap. Saba's verse in the song "Everybody's Something" increased his popularity. Saba continued rapping in 2013 and began to create his second mixtape, ComfortZone. The mixtape was released in July 2014. Saba used the album as a window into his life, produced the majority of the tracks on the project. He describes his surrounding and his optimistic attitude in his verses.^[5] The most popular song off ComfortZone was "Burnout" featuring Eryn Allen Kane.

2015–2017: Bucket List Project

Saba contributed to Chance the Rapper and Donnie Trumpet and the Social Experiment's debut studio album, Surf, by making a guest feature on its 10th song, "SmthnThtIWant". The album was released in May 2015 for free on iTunes. Saba released an instrumental EP called SpareChange! in 2015. The EP consists of 8 tracks available through SoundCloud. Toward the end of 2015 as well, Saba featured on Chance the Rapper's single "Angels". Chance the Rapper and Saba performed the song "Angels" on The Late Show with Stephen Colbert on Monday, October 26, 2015. Saba's popularity skyrocketed from his Stephen Colbert performance. The duo represented Chicago's radio stations, with sweatshirts reading "107.5 WGCI" and "Power 92.3" for the performance.

In January 2016, Saba released the single "GPS" featuring his father and musical influence, Chandlar. The single was included in his debut album, Bucket List Project, released on October 27, 2016. The album consists of 13 tracks featuring a wide array of other Chicago-based artists such as Noname, Twista, Akenya, Jean Deaux, and his brother Joseph Chilliams. The album focuses on his upbringing on the West Side and spirituality.^[7] In July 2016, Saba also appeared on Noname's debut album, Telefone, on the song "Shadow Man" alongside Phoelix and Smino.

In 2017, Saba released singles titled "Monday to Monday", "There You Go", and "Where Ideas Sing", however, had not announced a subsequent project for these songs. "Where Ideas Sing" was released on September 28, 2017. Shortly after, September 29, Artwork for the song was featured in downtown Chicago near Apple's new Apple Store on Michigan Avenue. The artwork was to promote both hometown artists Saba and Matthew Hoffman, who created the visual representation of Saba's lyrics.

In late 2017, after the tragic passing of cousin and fellow Pivot Gang member John Walt, Saba and Walt's mother Nachelle started the John Walt Foundation in his memory.^[8]

2018–2020: CARE FOR ME

On February 27, 2018, Saba released the track "BUSY", shortly after announcing a tour for his second album CARE FOR ME.^[9] He released CARE FOR ME on April 5, 2018, with tracks featuring Chance the Rapper, Kaina, and theMIND.^[10] Put together by producers daedaePIVOT, Daoud, and Saba himself, the album is dedicated to his late cousin and close friend Walter Long Jr. aka John Walt; who was fatally stabbed due to a situation on the train in Chicago in February 2017. Walter is heavily mentioned in the songs: "BUSY", "LIFE", and "PROM/KING". the latter recounts the events that Saba and Walter shared with each other leading up to Walter's death.^[11]

Saba was named one of 10 "Chicagoans of the Year" by the Chicago Tribune on December 27, 2018, for his music and his contributions to the John Walt Foundation, a foundation named in Walter Long's memory launched by Saba and Long's mother in 2017 to "foster the arts for Chicago youth".^[12]

Saba and the other members of Pivot Gang released their debut album, You Can't Sit With Us on April 19, 2019.^[13]

2021–present: Few Good Things

On May 21, 2021, Saba featured on the Audrey Nuna single "Top Again" off the album A Liquid Breakfast, along with making an appearance in the associated music video.^[14]

On November 4, 2021, Saba announced his third album Few Good Things and released the first single titled "Fearmonger".^[15] On November 18, he released the second single titled "Stop That".^[16] On January 13, 2022, he released the third single "Come My Way" featuring Krayzie Bone.^[17] The fourth single "Survivor's Guilt" featuring G Herbo was released on January 27.^[18] The album was released on February 4, 2022, including guest appearances from Black Thought, G Herbo, Krayzie Bone, 6lack, Smino, Mereba, Fousheé, Eryn Allen Kane, Cheflee, and Pivot Gang.^[19]

Saba was part of the lineup for the 22nd Coachella Valley Music and Arts Festival in April 2023.^[20]

Influences

Saba was influenced by his father, a Chicago R&B artist named Chandlar, at a young age.^[21] Chandlar would bring Saba to the studio with him to record sounds of soul, R&B and jazz.

Saba credits fellow Midwest musicians Lupe Fiasco, Bone Thugs-n-Harmony, and Kanye West as his biggest influence. Bone Thugs-n-Harmony got Saba into rap and made him want to write raps himself.^[5]

Saba was also influenced by his family members, most notably his older brother and late cousin. His brother is a rapper who goes by the stage name Joseph Chilliams and his cousin was a rapper who went by John Walt. Together, Saba's family and friends, are the backbone of the rap crew Pivot Gang. Pivot Gang is named after the famous scene in Friends where Ross, Rachel, and Chandler move a couch up the stairs and Ross continuously yells, "pivot." To the rap crew it means "to take things one step at a time and to always progress."^[22]

Studio albums

Mixtapes

Compilation albums

Extended plays

Singles

Guest appearances

Notes