Songfacts®:

• This song is about overcoming obstacles and working with what life gives you. Winwood emerged as a successful solo artist in the '80s after struggling with personal problems, including a divorce.
• Winwood wrote this song with the lyricist Will Jennings, who worked on most of Winwood's solo hits.
• Winwood's biggest solo hit in the US, this spent four weeks at #1 and also topped the pop chart in his native Britain. The album of the same title also topped the US albums chart.
• The Memphis Horns played on this song, giving it a brassy Motown feel. Motown Records thought the song was too similar to the 1966 track "(I'm A) Road Runner" by Jr. Walker & the All Stars, released on Motown's subsidiary Soul Records. After legal action, the writers of "(I'm A) Road Runner" - Lamont Dozier, Brian Holland and Eddie Holland - were added to the credits of "Roll With It."
• Winwood was 40 years old when this went to #1 in America in July 1988. The older crowd was well represented in pop music at this time - Chicago, George Harrison and The Beach Boys all had chart-toppers as well. It was a time when older-skewing songs like "Roll With It" could share space on pop playlists with the likes of Michael Jackson, Whitney Houston and Poison.
• This song holds the distinction of being the last #1 song of Casey Kasem's 18-year run as original host of the American Top 40 radio show (he would rejoin the show 10 years later) - and the first #1 song for the show under Kasem's successor, Shadoe Stevens. >>>

  Suggestion credit:
  Joshua - Twin Cities, MN
• David Fincher, whose later directed the films Seven, The Curious Case of Benjamin Button and Gone Girl, directed the music video.