5 Flop Songs From The '00s That Belong On Every Road Trip Playlist

For artists and celebrities, perhaps there's nothing more terrifying than being in your "flop era," the moment in a career when someone respected falls below the high expectations of what they can do. The good thing is, as with anything in life, it's not permanent, and sometimes, a song is a flop just because people aren't ready for what the artist is putting out there.

Billboard's digital download chart and iTunes' chart both debuted in the mid-2000s, marking the transitional era between physical and streaming music. So, perhaps it was easier to become a flop then than it is now. You needed good marketing, management, and the right audience all at the same time to ensure success. In this sense, "flop" doesn't mean bad; in fact, all of the songs on this list are great. Rather, it refers to how poorly they performed on the charts. All of these songs fell short of expectations based on the artist's previous releases or even compared to the success of other singles from the same album. While they all fell through the cracks at the time, several of these found a second life after their initial release.

So, how did we pick these five flop songs from the 2000s that belong on every road trip playlist? First, we looked at Billboard and worldwide charts to see how they performed; none of these songs cracked the top 20 in the U.S. and had minimal impact elsewhere. We also picked songs that fit one of three necessary road trip vibes: songs that you can sing along to, cruise along to, or just vibe out to. Combine these with these flop '80s songs that are a must for any road trip, and you'll be set to drive cross-country without a hitch.

Unless you're a queer person, Britney's masterpiece "Blackout" may have flown under your radar. Besides "Gimme More," which peaked at #3 on the Billboard Top 100 in 2007, "Blackout" didn't deliver the massive hits the Princess of Pop was known for, despite being a perfect album. 2007 was a difficult year for Spears: she shaved her head, delivered a much-criticized VMA performance of "Gimme More," and went to rehab. All of this overshadowed the October release of "Blackout," her first album not to debut at #1 (although #2 isn't so shabby).

The third single, "Break the Ice," begins with a classic Britney whisper: "It's been a while / I know I've kept you waiting / but I'm here now," before launching into a dark, hard-hitting beat produced by Danja. He was the vision behind the album's gritty, distorted sound that changed the direction of pop music and pushed it to a "hard 808 hip-hop urban appeal," as he told The Fader in 2017. "Blackout's" sound influenced artists like The Weeknd and Charli XCX, the latter of whom named it her favorite album of all time.

"Break the Ice" is perfect for cruising along the scenic stops from Zion to Vegas, where you can scream to it while wooing with your arms in the air. Or queue it up for a late-night drive when you need a bit of Britney, b–ch, for energy. "Break the Ice" peaked at 43 on the Billboard Top 100 and charted for 17 weeks, which is low for Britney. It currently has over 99.3 million streams on Spotify (compared to "Gimme More's" 1.1 billion). It may be a "flop" in numbers compared to all of her number 1 hits, but sonically and culturally, it's not a flop at all.

It feels like sacrilege to call anything from Red Hot Chili Peppers' massive global hit "Californication" a flop, but considering just how big some of the album's singles were, that's what "Road Trippin'" is by comparison. While the album came out in June 1999, "Road Trippin'," the album's fifth single, came out in December 2000 and was only released in Australia and Europe, peaking at #30 in the U.K. in 2001. It's a far cry from other singles from the album, like "Californication," which may have only reached #16 on the U.K. charts but hit #1 in the U.S. (as did "Scar Tissue"). The song "Californication" has also had a resurgence in the streaming era, with over 1.9 billion streams on Spotify and 1.3 billion views on YouTube to date.

"Road Trippin'" is a rare RHCP song that's performed totally acoustic, without Chad Smith's energy on the drums. If you want to immerse yourself fully in it, drive up the Pacific Coast Highway to the striking cliff views of Big Sur, watching how the blue Pacific Ocean sits "so pretty west of the 1 / sparkles light with yellow icing, just a mirror for the sun," as Anthony Kiedis gently sings. With its mix of acoustic guitar and strings, "Road Trippin'" is perfect for a California road trip. After all, RHCP is a quintessential California band, so add it to your playlist while driving the most breathtaking road trip routes on the West Coast.

"Road Trippin'" has found a new life in the streaming era; currently, it has over 243 million listens on Spotify, making it the fifth most-listened-to track on the album, and 44 million views on YouTube.

2006 was the year of Gnarls Barkley, whose "Crazy" was the most ubiquitous tune of the year. Rolling Stone named it the top song of the decade, calling it "the most glorious pop thrill of our time." Comprised of CeeLo Green and producer Danger Mouse, Gnarls Barkley was an imaginary persona who supposedly taught Kraftwerk English and counted Mariah Carey and Janet Jackson among their exes. CeeLo, who was known as an R&B artist, found the perfect vehicle for his smooth voice with Danger Mouse's beats. Together, the two made "boundary-defying" pop tracks unlike anything else on the charts at the time, blending soul with psychedelic rock.

After the massive success of "Crazy," which hit #2 on the Billboard Top 100 and stayed on the charts for 29 weeks, the band released "Smiley Faces," the second single from their Grammy Award-winning album, "St. Elsewhere." "Smiley Faces" was nowhere near as successful as "Crazy." It had a brief stint in the top 10 charts in the U.K. and Ireland and didn't fare well elsewhere, either. It never cracked the top 20 in Europe (besides Portugal) or Australia, and it wasn't even released as a single in the U.S.

It's a shame, because it's a fun, energetic song that makes you smile and just want to move your body. It's perfect for a road trip, as it brings something upbeat and unexpected to the mix, probably won't get stuck in your head for the next 20 years, and allows you to practice a falsetto so high that only dogs can hear it. Be sure to queue it up for a road trip to CeeLo's hometown of Atlanta, where you'll find queer-friendly neighborhoods filled with mouth-watering bites.

The late 2000s was the era of "indie sleaze." a time of hipsters photographed by the Cobrasnake in their Sebastian Tellier-designed tees and apathetic party vibes. Songs like Animal Collective's "My Girls," MGMT's "Kids," and Crystal Castles' "Crimewave" provided the perfect soundtrack for these sweaty, American Apparel-clad indie crowds in Coachella dance tents. And then there was Santigold's (f.k.a. Santogold) hit "L.E.S. Artistes" off her then-eponymous debut, which offered a biting critique of trying to be creative among New York's Lower East Side (L.E.S.) hipsters pretending to be artists.

A former A&R exec and songwriter for pop girls like Ashlee Simpson, Santigold found success with "L.E.S. Artistes," which peaked at 27 on the U.K. charts and was widely seen as one of the best songs of the 2000s, with Rolling Stone ranking it #69 in the top 100 songs of the decade. And while the third single, "Lights Out," was also critically acclaimed, it barely made a dent on the U.K. charts, peaking at 43 and only staying on for three weeks.

"Lights Out" is a great driving song that captures an '80s new wave vibe that could perfectly accompany a drive on America's most historic road trip. In the album review, Pitchfork describes the song as finding a "fascinating middle ground between the Pixies and the Go-Go's." Later that year, the publication named it one of the best tracks of 2008, saying that while it may sound familiar, the song "doesn't really sound like anything else other than a wizened, longtime industry vet finally writing songs for herself." While "L.E.S. Artistes" has 80.4 million streams on Spotify, "Lights Out" is just at 18.7 million, meaning it's waiting to be discovered by a new generation of road trippers.

Arguably, Sia is the pop voice of the 2010s, leaving her mark on some of the decade's biggest songs. David Guetta's 2011 smash hit "Titanium" has 2.1 billion views on YouTube and 2.2 billion streams on Spotify, meaning a number equal to half of the planet's population has screamed to Sia's rousing "I am titanium!" Then there's her decade-defining 2012 single "Chandelier," with 2.2 billion listens on Spotify and a staggering 2.9 billion views on YouTube. So, how can one of the biggest pop stars on Earth ever be called a flop?

Sia started out as a lesser-known indie singer in the 2000s. "Breathe Me," the first single of her 2004 album, "Colour the Small One," only reached 71 on the U.K. charts, and the song didn't make an impact in the U.S. until 2005, when it appeared in the final scene of "Six Feet Under." Claire Fisher (Lauren Ambrose) drives away from home, seeing the future deaths of everyone on the show, as Sia's aching vocals bring the already emotional scene to an 11. "Breathe Me" became indelibly linked to setting out on an unknown journey and the pain of loss. It's an essential road trip playlist addition, particularly if you want a haunting soundtrack while exploring the best ghost towns of the Pacific Northwest.

The album was re-released in the U.S. in 2006, and while Rolling Stone named the song as a highlight, it only gave the album 2.5 stars. "Breath Me" never came close to the success Sia found later, itself a result of the burnout from her indie career. Her struggle as a solo artist led her to transition to pop music, writing songs for Beyoncé and Rihanna before becoming a pop star herself, which breathed a second life into "Breathe Me," which has over 426 million streams on Spotify.

As a 30-something who was in her teens and 20s in the 2000s and who has taken many road trips in her life (although America's most iconic road trip remains unchecked on my bucket list), I started with my own experience. What was the 2000s music I loved, and what type of music works best for a long drive? For me, it's music that energizes you as you sing along with it or harmonize with your friends (or dog) in the backseat. It's also atmospheric music that you can space out to, or that fits the scenery. 

I chose songs across different genres to get a bigger scope of the decade and then narrowed the list down by chart performance. While some of these had an impact abroad, it was short-lived and minimal, so these are all songs that generally underperformed on the U.S. charts. I determined performance by looking at songs that didn't crack the top 20 at the time of release. This question of "performance" was also determined by expectations for the artist; one wouldn't expect a Britney song to peak in the 40s on the charts or for the follow-up to Gnarls Barkley's "Crazy" to be anything but a top 10 hit. An artist's later career was also considered, like Sia's massive success as a pop star versus her start as an indie singer.

I used sites like Billboard and  Official Charts (for U.K. releases) to determine chart performances, while Rolling Stone, Pitchfork, and The Guardian offered the critical takes needed for more context on how they were received. I also looked at the year-end and decade-focused lists of Rolling Stone, Pitchfork, and NME to see how these songs fared critically, both at the time and later.