‘Winning Streak’ Review: Jelly Roll’s Got Himself a Winner

After a year of smaller collaborations and features, Jelly Roll has returned to the country charts with his tenth studio album, “Beautifully Broken.” Though “Winning Streak” is not its lead single, the song is a strong opening track for the album and an even stronger example of musical storytelling.

In a recent podcast episode of “Sunday Sitdown with Willie Geist,” Jelly Roll revealed that “Winning Streak” was inspired by an exchange he witnessed between two people at an Alcoholics Anonymous meeting. In the song, a newcomer breaks down in tears and is comforted by an older man who has been sober for twenty years. The older man reminds the newcomer, “Nobody walks through these doors on a winning streak.”

The song is in first-person perspective, providing a deeply intimate window into Jelly Roll’s personal struggles with alcoholism and addiction. The rapper-turned-country singer has been open in past releases and interviews about his mental health challenges. However, according to a new interview with The New York Times, “Winning Streak” marks the first time that Jelly Roll has spoken publicly about attending Alcoholics Anonymous meetings himself.

The lyric “Hello, my name’s Jason” is a particularly striking reference to the standard introduction among attendees of Alcoholics Anonymous meetings, swiftly spotlighting substance abuse as a major theme of the album. The use of Jelly Roll’s real first name makes the lyrics even more vulnerable.

The storytelling in “Winning Streak” complements this vulnerability by putting listeners directly in the narrator’s shoes. In just one verse, Jelly Roll paints a picture of someone desperate for help. Poignant details such as “sweatin’ in an old church basement” hint at the challenging symptoms of alcohol withdrawal as well as the deep-rooted fear of asking for help. The song also features clever wordplay like, “wanna quit quittin’,” which encapsulates the inner turmoil involved in battling addiction.

Though outshined by Jelly Roll’s songwriting, the gospel-inspired instrumentals of “Winning Streak” offer a refreshing contrast to current musical trends. Dramatic background vocals and generous reverb add an airy, expansive sound that complements the artist’s emotional singing. Like many of today’s hits, however, the song cycles through the same four chords, missing out on a prime opportunity for exciting or unexpected modulations that would match the vocal drama.

In the context of the album “Beautifully Broken,” the single “Winning Streak” is everything an opening track should be. The song immediately establishes the project’s focus and sets a high bar for what follows.

When asked about the impetus for writing the track, Jelly Roll explained, “I think that our responsibility as songwriters too, sometimes, is to tell the stories that aren’t being told.”

“Winning Streak” embraces this responsibility with pride. Spearheading Jelly Roll’s promising return to country stardom, this release transforms a private, painful experience into an uplifting message of solidarity and hope for all.

—Staff writer Audrey H. Limb can be reached at audrey.limb@thecrimson.com.