In the 2000s, we weren’t as focused on whether songs were “PC” as we are today. So there are countless 2000s hits with questionable lyrics that were completely acceptable at the time. Among them are these four hits of the 2000s that haven’t aged well.
“TiK ToK” By Kesha
Released in August 2009, at the tail end of the 2000s, this hit’s opening line hasn’t aged well. “Wake up in the mornin’, feelin’ like P. Diddy.” At the time, P. Diddy was considered one of the biggest names in rap and hip-hop, and many longed to live a life like his. Ultimately, that mentality didn’t hold up. On September 16, 2024, Sean “Diddy” Combs was arrested on charges of racketeering conspiracy, sex trafficking, and transportation to engage in prostitution.
“Picture To Burn” By Taylor Swift
Taylor Swift was bold on her debut album, including a track with a now-homophobic song lyric. At the time, calling someone “gay” was an insult, as society hadn’t yet grown to accept gay people. In her fourth single, “Picture To Burn”, Swift used the word as an insult toward her ex-boyfriend from high school. In the song, she sang, “So go and tell your friends that I’m obsessive / That’s fine, I’ll tell mine that you’re gay.” Swift later changed this line to “I’ll tell mine you’re going nuts” when re-recording the track for her entirely re-recorded debut album, released in May 2025.
“Ur So Gay” By Katy Perry
Taylor Swift wasn’t the only one who earned a hit containing homophobic lyrics. In 2007, Katy Perry released “Ur So Gay”, mocking her former partner’s metrosexuality. Though Swift’s track only barely uses the word “gay” as a quick insult, Perry penned an entire song about questioning her ex’s sexuality. Perry opens the track with the lyrics “I hope you hang yourself with your H&M scarf while jerking off, listening to Mozart”. There are multiple reasons why these opening lines didn’t age well, including homophobia and telling someone you hope they kill themselves. All around, this one didn’t age well.
“A Milli” By Lil Wayne
In 2008, Lil Wayne penned one of his biggest hits, “A Milli”. His 2008 album, Tha Carter III, debuted at No. 1 on the Billboard 200. He earned back-to-back No. 1 hits on the US Hot R&B/Hip-Hop Songs chart, with “Lollipop” and “A Milli”. The latter contained lyrics that didn’t age well immediately, but rather over time. In “A Milli”, Lil Wayne stated, “And I’d rather be pushin’ flowers than to be in the pen sharin’ showers”. It’s pretty obvious what the rapper meant by this, but shortly after its release, Lil Wayne was convicted on gun charges. He was then sent to Rikers Island, a prison on the East River in New York City.
Photo by Michael Buckner/ACMA/Getty Images for ACMA
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