On this day in 1988: Steve Winwood started a four week run at #1 on the U.S. singles chart with ‘Roll With It’, a #53 hit in the U.K. Later, Motown songwriters Holland-Dozier-Holland were credited with co-writing the song due to its resemblance to the Junior Walker hit (I’m a) Roadrunner.

The song spent four weeks at #1 on the Billboard Hot 100  singles chart in the summer of 1988.  It topped the Billboard Adult Contemporary Chart for two weeks, and also spent four weeks at #1 on the Billboard Mainstream Rock Chart. In addition, the song reached #30 on the R&B Chart.

“Roll with It” was nominated for two Grammy Awards in 1989, Record Of the Year and Best Male Pop Vocal Performance. The album Roll with It was also nominated as Album of the Year.

The song was the last #1 hit of Casey Kasem’s 18-year run as the original host of American Top 40 (he would return to host the program 10 years later), as well as being the first #1 song of Shadoe Stevens’ hosting tenure.

The music video, directed by David Fincher and filmed in sepia-tone, depicts Winwood performing the song in a bar.

Here’s a look at the complete Top 10 on the U.S. singles chart from this day in 1988:

1 4 ROLL WITH IT –•– Steve Winwood – 8 (1)
2 1 HOLD ON TO THE NIGHTS –•– Richard Marx – 11 (1)
3 6 HANDS TO HEAVEN –•– Breathe – 16 (3)
4 2 POUR SOME SUGAR ON ME –•– Def Leppard – 15 (2)
5 7 MAKE ME LOSE CONTROL –•– Eric Carmen – 11 (5)
6 9 SIGN YOUR NAME –•– Terence Trent D’Arby – 10 (6)
7 3 NEW SENSATION –•– INXS – 12 (3)
8 11 1-2-3 –•– Gloria Estefan & Miami Sound Machine – 9 (8)
9 10 RUSH HOUR –•– Jane Wiedlin – 13 (9)
10 14 I DON’T WANNA GO ON WITH YOU LIKE THAT –•– Elton John – 7 (10)