Justin Timberlake is taking a trip down memory lane with Complex, revisiting some of the biggest songs of his career and deciding which ones deserve the top spots. In a new episode of Complex’s Re-Rank, hosted by Jordan Rose, Justin sits down to discuss Complex’s ranking of his 10 best songs, sharing the stories behind some of his most memorable records before putting together a personal top 10 of his own.
Following Complex’s list of The 30 Best Justin Timberlake Songs of All Time, Ranked, Justin is getting the chance to weigh in on the rankings himself. In the latest episode of Re-Rank, hosted by Jordan Rose, he revisits some of his biggest hits, shares stories behind the songs, and reveals his own personal top 10 favorites.
The challenge wasn’t an easy one for Justin, who admitted right from the start that choosing his favorite songs was practically impossible. As a songwriter, he explained that he loves each track for different reasons, depending on where he was in his life and what he was exploring creatively at the time. Growing up in Memphis and surrounded by different styles of music also played a big part in shaping how he approaches songwriting.
Complex kicked things off with its ranking of Justin’s greatest songs, placing “Cry Me a River” at No. 1, followed by “My Love” and “Like I Love You.” While Justin was willing to go along with some of the choices, he had a few songs in mind that he felt deserved to climb higher.
During the conversation, Justin shared some interesting details about the making of several classics. He revealed that “Cry Me a River” came together in just 5 to 10 minutes, with the vocals recorded in approximately two hours. He also talked about the experimental sound of “My Love” and how he and Timbaland approached creating something that didn’t necessarily follow the usual rules.
One of the highlights was hearing Justin revisit “Mirrors,” a song inspired by the relationship between his grandparents, whose lifelong commitment left a lasting impression on him. Interestingly, he revealed that he originally wrote the track on the same day he and Timbaland worked on “Carry Out,” but it sat unfinished for almost five years before they returned to it for The 20/20 Experience.
Justin also reflected on the impact of “SexyBack,” explaining how he and Timbaland wanted to redefine dance music with a rock-and-roll mentality. Despite initially being told by the label that the song wouldn’t work, Justin trusted his instincts. He even recalled wanting listeners to hear the record without immediately recognizing his voice. Looking back, he considers it an important moment of trusting his creative instincts and doing something completely different.
There were plenty of other memorable stories, too. Justin revisited the history of *NSYNC’s “Gone,” revealing that the song was originally written with Michael Jackson in mind. After Michael heard the track, he contacted Justin about recording it as a duet. However, Justin ultimately decided to keep his commitment to his group and the version that had already been released on Celebrity.
He also explained that “What Goes Around…Comes Around” was inspired by a friend’s personal experience rather than his own, and discussed the influence of “Rock Your Body,” including Don Toliver’s use of the song in his track “Body.” Justin even shared that his son, Silas, encouraged him to approve the sample.
Complex’s Ranking of Justin Timberlake’s Top 10 Best Songs
Before Justin got to rearrange the list, Complex’s music team presented its picks for his 10 best songs, spanning his solo career and his time with *NSYNC.
- “Cry Me a River”
- “My Love”
- “Like I Love You”
- “Mirrors”
- “SexyBack”
- “Rock Your Body”
- “What Goes Around…Comes Around”
- “Gone” (*NSYNC)
- “Señorita”
- “Suit & Tie”
Justin Timberlake’s Ranks His Top 10 Songs of All Time
After working through Complex’s ranking and making a few adjustments, Justin was given the opportunity to share his own personal top 10 without any rules or restrictions. He even came prepared with notes!
While he admitted that his choices weren’t necessarily in a strict order, he settled on a list led by “What Goes Around…Comes Around,” followed by “Mirrors” and “My Love.”
Here’s how Justin ranked his personal favorites:
- “What Goes Around…Comes Around”
- “Mirrors”
- “My Love”
- “SexyBack”
- “Cry Me a River”
- “Rock Your Body”
- “Until the End of Time”
- “Pusher Love Girl”
- “Strawberry Bubblegum”
- “LoveStoned”
It’s especially fun seeing “Strawberry Bubblegum” make the cut, with Justin even giving the song a little shoutout earlier in the conversation when discussing tracks he felt deserved more attention.
The interview also wrapped up with a little tease about what might be coming next. With the 20th anniversary of FutureSex/LoveSounds being celebrated, Jordan asked Justin what fans could look forward to. Justin confirmed that he and longtime collaborator Timbaland are still working together, adding that they’ve been creating music from scratch. He wasn’t giving too much away, but he did say he’s been “cheffing.”
My Ranking of Justin Timberlake’s Top 10 Best Songs
Of course, I had to share my own favorites! Here’s my personal top 10, featuring a mix of solo classics and a couple of more recent favorites.
- “Cry Me a River”
- “SexyBack”
- “My Love”
- “Tunnel Vision”
- “What Goes Around…Comes Around”
- “LoveStoned”
- “Rock Your Body”
- “Technicolor”
- “FutureSex / LoveSound”
- “Drown”
Watch Justin revisit his musical catalog, share some of the stories behind his biggest hits, and reveal his personal top 10 in the full Complex Re-Rank interview below!
Justin Timberlake Ranks His Best Songs on Complex’s Re-Rank
