What Was the Number One Song in August 1988

Title: Exploring the Chart-Topping Hit of August 1988: Unraveling the Number One Song of the Era


Music has always played a significant role in capturing the essence of an era. The songs that dominate the charts often become the soundtrack of our lives, evoking memories and emotions for years to come. In August 1988, one particular song stood out among the rest, captivating listeners worldwide. In this article, we dive into the history and significance of the number one song of August 1988, its impact, and its enduring popularity.

The Number One Song in August 1988: “Roll With It” by Steve Winwood

In August 1988, “Roll With It” by Steve Winwood claimed the coveted number one spot on the Billboard Hot 100 chart. Released as the lead single from his album of the same name, the song showcased a captivating blend of pop, rock, and R&B elements. With its infectious groove, catchy hooks, and Winwood’s soulful vocals, “Roll With It” quickly became a fan favorite.

The Song’s Impact and Reception:

“Roll With It” dominated the charts for four consecutive weeks, solidifying its place as a defining hit of the late ’80s. The song’s success catapulted Steve Winwood back into the limelight, reminding the world of his remarkable talent as a singer-songwriter and musician. Its upbeat tempo and positive message resonated with listeners, making it a staple of radio playlists and dance floors alike.

11 Common Questions and Answers:

1. Who wrote “Roll With It”?
“Roll With It” was written by Steve Winwood and songwriter Will Jennings.

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2. What inspired the creation of the song?
The song’s lyrics revolve around optimism and resilience, encouraging listeners to persevere through adversity. It is believed that personal experiences and the challenges faced by Winwood in the music industry inspired the uplifting message of the song.

3. Was “Roll With It” Steve Winwood’s only number one hit?
No, Steve Winwood had previously achieved success with hits like “Higher Love” and “Valerie.” However, “Roll With It” was his only song to top the charts in the United States.

4. How did “Roll With It” compare to other songs of that era?
“Roll With It” showcased the fusion of pop, rock, and R&B that was popular in the late ’80s. Its infectious groove and catchy chorus made it a standout track among the numerous hits of the time.

5. Did “Roll With It” win any awards?
While “Roll With It” did not win any major awards, it received critical acclaim and solidified Steve Winwood’s reputation as a talented artist.

6. Did the success of “Roll With It” impact Steve Winwood’s career?
Yes, “Roll With It” revitalized Steve Winwood’s career, introducing him to a new generation of fans and reaffirming his status as a respected musician.

7. How did the song resonate with listeners?
“Roll With It” resonated with listeners due to its positive message and infectious energy. The song’s relatable lyrics and catchy melody made it an instant favorite, earning it widespread popularity.

8. Did “Roll With It” have any cultural impact?
While “Roll With It” did not have a significant cultural impact, it remains an iconic song from the late ’80s and represents the vibrant music scene of that era.

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9. Did “Roll With It” inspire any covers or remakes?
While there haven’t been notable covers or remakes of “Roll With It,” the song remains a beloved classic in Steve Winwood’s discography.

10. How does “Roll With It” hold up today?
Even after over three decades, “Roll With It” remains a timeless hit. Its catchy melody and uplifting message continue to resonate with listeners, making it a popular choice on classic hits radio stations.

11. What is Steve Winwood’s legacy?
Steve Winwood’s legacy extends beyond “Roll With It.” With a career spanning over five decades, he has left an indelible mark on the music industry, delivering numerous hits and contributing to the growth and evolution of rock, soul, and pop genres.


“Roll With It” by Steve Winwood was undoubtedly a standout hit in August 1988. Its infectious groove, positive message, and Steve Winwood’s soulful vocals made it an unforgettable song of its era. Even today, the timeless appeal of “Roll With It” continues to captivate audiences, solidifying its place in music history as a defining hit of the late ’80s.