Cool Relax

Cool Relax was the follow-up to his 1995 debut Bonafide. Jon assumed the role of having more creative control on his second album. On his debut, he was given leeway to write and produce, but Edmonds and her then-husband Babyface were heavily involved in the making of Bonafide.[2] Jon was confident in the material for his new album, but fought with Edmonds and Babyface over certain songs to keep on the project.[2]

Aside from his work, Jon sought outside production from Tim & Bob, Johnny J, David Foster and Ali Shaheed Muhammad of A Tribe Called Quest, among others. The song that became the first single "Don't Say", was written by former Boyz II Men and Az Yet member Marc Nelson. Jon overheard Nelson playing the song in the record company's parking lot and asked to record it for his album.[2] The music video for the single featured a then-unknown Sanaa Lathan as the female love interest.[3]

"They Don't Know" was released as the next single, with a music video directed by Christopher Erskin.[4] The song's B-side "Are U Still Down" was also issued despite objections from the record company, as it featured vocals from the then-deceased Tupac Shakur who died when Jon started recording the album.[2] Jon received assistance from Shakur's mother Afeni Shakur, who gave Jon permission to clear his vocals for the song.[2] He would record a sequel to "Are U Still Down" called "Part 2" with a posthumous appearance by Shakur on his 2004 album Stronger Everyday.

The next single was the song "I Do (Whatcha Say Boo)". The song originally appeared on his demo tape prior to recording Bonafide- as did the album track "Can We Get Down".[2] The final single was the title track, which had a remix that featured Guru from the hip hop group Gang Starr. The song was produced by Ali Shaheed Muhammad, who Jon sought out due to being a longtime fan of A Tribe Called Quest.[2] "Pride & Joy" was originally recorded by Toni Braxton for her sophomore album Secrets, but the song never made the final track listing.[2] Jon later recorded the song for himself, while giving her the song "In the Late of Night" for her album.

The last song on Cool Relax- "Tu Amor"- was penned by songwriter Diane Warren.[2] Jon felt the song didn't fit in with the rest of the album and was done at the request of Epic Records in seeing the potential of the song becoming a huge hit.[2] Almost a decade later, the song would be covered by Mexican pop group RBD for their English language album Rebels.[5]

One song that didn't make the track list was "Paradise in U".[2] A little over a decade later, he included the song on his 2008 album Helpless Romantic.[6]

Credits adapted from liner notes[7] and Allmusic.[8]

Credits adapted from liner notes[7] and Allmusic.[9]