The album features guest appearances from Drake, Kanye West, E-40, Chris Brown, Ty Dolla Sign, Jhené Aiko, Lil Wayne, and Ariana Grande, while the production was handled by a variety of collaborators, including Kanye West, DJ Mustard, DJ Dahi and Key Wane, who also serves as the album's executive producer alongside Big Sean himself.

The album was supported by five singles: "I Don't Fuck with You", "Paradise", "Blessings", "One Man Can Change the World" and "Play No Games".

Dark Sky Paradise received generally positive reviews from critics, who praised the change in Sean's production and lyricism being more atmospheric and substance-filled.

[2] "One Man Can Change the World" featuring Kanye West and John Legend, was sent to rhythmic contemporary radio on June 19, 2015, as the album's fourth single.

[2] "Play No Games" featuring Chris Brown and Ty Dolla Sign, was sent to urban contemporary radio on September 22, 2015, as the album's fifth single.

[10] John Kennedy of Billboard said, "With sterling wordplay and a consistent melancholy vibe, the Detroit native took all the tension, the highs and lows, and laid it out on wax, compiling the strongest project of his career".

[11] Justin Charity of Complex said, "Occasionally clumsy but wonderfully plainspoken, and impassioned when he wants to be, Sean has advanced (if not graduated) from the tepid mythmaking of Hall of Fame.

[13] Jon Caramanica of The New York Times said, "In the last year, he's made real strides toward lucidity, and on Dark Sky Paradise, his third and best album, he is more human than ever before".

[17] Dark Sky Paradise debuted at number one on the US Billboard 200, with 173,000 album-equivalent units (including 139,000 copies as pure albums sales) in its first week.