The original version of this song was three verses that Cole rapped over a Tupac beat. It started coming to life at a private show in L.A., where during the sound check Cole and his band decided to add a little jam session for the fans. The keyboard player played to a beat that Cole had made with a Jennifer Hudson sample and the rapper realized straight away that it completely fitted with the first verse on "Crooked Smile". Cole's right hand man Ibrahim "IB" Hamad recalled to Vibe
magazine: "I've never been a part of a song that was worked on for as long as this one. it was incredible to see the transformation. Elite came in and co-produced the record with him and they really took their time on this record. I remember everybody watching a lot of Quincy Jones interviews and documentaries around that time. We all knew this record was special and it was treated that way by everyone involved.
"Once the hook was added," he continued, "Cole already had in his mind he wanted to work with TLC. It had a very 'Unpretty
' feel to it. The vibe of the record and the message was perfect for them."