His third studio album Merchants, Dealers & Slaves, which was released on 20 October 2013, received positive reviews from music critics and yielded the singles "Down" and "Eko".

In October 2014, Brymo released his fourth studio album Tabula Rasa; its lead single "Fe Mi" was described as a "soft traditional ballad".

In March 2018, Brymo released his critically acclaimed sixth studio album Oṣó, which includes a mixture of alternative folk and Yoruba music, and spawned the singles "Heya!"

[5][6] Brymo teamed up with three members of Skata Vibration to form A.A.A, an alternative rock band whose eponymous debut Extended Play (EP) was released in August 2019.

He has released books Oriri's Plight (2018), Verses (2020) and The Bad Tooth (2022), and starred in the films Price of Admission (2021) and Elesin Oba, The King's Horseman (2022).

Olawale Ashimi was born and raised in Okokomaiko, Ojo, Lagos State, Nigeria; his father is an Awori carpenter and his mother is an Egun petty trader; he is his parents' only child.

[12] Ashimi gained admission to Lagos State University (LASU), where he studied zoology, but after his second year he left to pursue a career in music.

[9] In a 2013 interview with The Sun, Brymo said management problems prevented him from getting a marketing deal for the album and that he had a one-million naira offer that failed because of technical issues.

[7] On 15 November 2012, Brymo released his second studio album The Son of a Kapenta,[10] which includes guest appearances from Jesse Jagz, Pryse, M.I, Ice Prince and Efya.

[9] In a July 2012 interview with Adeola Adeyemo of BellaNaija, Brymo said he recorded the song while being under pressure from Chocolate City to submit a single.

[20] In a 2012 interview with newspaper The Punch, Brymo said his father's carpentry profession inspired the album's title, described The Son of a Kapenta as a summary of his life and said each song is a reflection of his energy.

[22] On 20 October 2013, Brymo released his third studio album Merchants, Dealers & Slaves,[23] which was produced by Mikky Me and includes guitar work from David.

[26] In May 2014, Nigerian Entertainment Today reported undergraduate students at Southern Illinois University Carbondale had examined the lyrics of "Down" as part of a case-study project.

[34] "Fe Mi" was released as the album's lead single on 18 September 2014;[35] Ayo Onikoyi of Vanguard described the song as "a soft traditional ballad".

[39] In an interview with newspaper This Day, Brymo said the project's script inspired the song and that he was interested after Wakaa's production team contacted his management.

[43] Audu Maikori, who was CEO of Chocolate City, refuted Brymo's claims during a press conference at the label's office in Lekki.

[44] According to newspaper Vanguard, during the press conference, Maikori said Brymo had committed an act of insubordination when he refused to remove a picture he posted on Instagram.

[46] Nigerian Entertainment Today reported Spinlet discontinued the deal after Chocolate City made them aware of the label's existing contract with Brymo.

[47] On 14 October 2013, Chocolate City filed an interim injunction against Brymo, restraining him from partaking in musical ventures beyond the confines of his contract.

[50] On 21 October, a judge at the Federal High Court of Lagos restrained Brymo from releasing and distributing any musical work pending Chocolate City's lawsuit against him.

[66] The video received mixed reviews; in an e-mail to Pulse Nigeria, Brymo defended his decision to expose his buttocks, saying; "I decided to appear how my forebears dressed before the arrival of civilization to Nubian continent".

[68] In 2019, Brymo teamed up with three members of Skata Vibration to form A.A.A, an alternative rock band that also included guitarist Jad Moukarim, drummer Adey Omotade, and bassist Laughter.

[82] Brymo made his acting debut in Udoka Oyeka's 2021 short film Price of Admission, in which he played Kola, a musician who struggles to get a record deal and attain fame.

[86] In a review for YNaija, Kola Muhammed said the EP is a "musical diary bearing tales of anguish" and that Brymo "sought to heal himself from the pain of defamation".

[86] Pulse Nigeria's Motolani Alake awarded the EP a rating of 8.2 out of 10, saying it is "largely about Brymo's journey back to life, as aided by love".

[94] In a review for The Cable Lifestyle, Fareedat Taofeeq awarded the album seven stars out of 10, calling it a "great piece" and commending Brymo for "maintaining his style and music direction over the years".

[96] Motolani Alake of Pulse Nigeria rated the album 9.9 out of 10, praising its production and acknowledging both artists for "assuming the positions of philosophers who examined the meaning of life as it relates to self, love, and loss".

[9] Brymo's albums Merchants, Dealers & Slaves and Tabula Rasa comment on social injustice and chaos that are prevalent in Nigerian society.

[105] In January 2023, Brymo announced on Twitter his support for Bola Tinubu in the 2023 Nigerian presidential election and said an Igbo presidency will remain a fantasy as long as there are talks about Biafra in the country's South East.

[107] A petition that was launched through Change.org and signed by over 40,000 people called for Brymo's nominations at the eighth annual All Africa Music Awards to be revoked.