Songfacts®:

• A song called "Smile," with a chipper tune and a lilting vocal by a 21-year-old British singer must be full of sunshine, right? That's not the case. Lily Allen is smiling because her cheating boyfriend is alone and suffering. It's what the Germans call "schadenfreude."
  
  The ex-boyfriend Allen is singing about is Lester Lloyd, a DJ she named as the song's inspiration. The song recounts his attempts to win her back after the terrible way he treated her.
  
  In the Sun newspaper, September 19, 2006, she describes performing the song at the Secret Garden Party: "The festival was well good, particularly as Lester (my ex, who I wrote 'Smile' about, and subsequently sold his story to the papers) had a tent positioned directly opposite the main stage. So he and his new girlfriend had no option but to watch me perform to a couple of thousand people singing 'Smile' back to me. Oh, it's the little things eh!"
• The organ part was sampled from the song "Free Soul" by the '60s reggae group The Soul Brothers.
• "Smile" was Lily Allen's first single, and it was an instant hit in her native UK. She performed the song on several TV appearances and other promotional events, including Top of the Pops and Saturday Night Live. At the 2007 South By Southwest (SXSW) music fest in Austin, Texas, Allen declared that she was "So sick of this song" before performing it.
• Lily was an inexperienced songwriter when she sat down with pop hitmakers Iyiola Babalola and Darren Lewis (Nicole Scherzinger, Shakira) to write this. She explained in Daniel Rachel's The Art of Noise: Conversations with Great Songwriters: "I remember writing the verse and the chorus and then them going, 'OK, we just need a middle eight,' and I was like, 'I don't know what that is.' So I had to run out of the studio and call my manager. I was so embarrassed."
  
  After her manager explained the middle eight was "that piddly bit in the middle that's not the verse and not the chorus but kind of links the two," she came up with a series of la, la, la's to fill the space.
• In the video, Allen takes revenge on an ex-boyfriend (played by EastEnders actor Elliott Jordan) in various ways, including hiring gangsters to beat him up and spiking his coffee with laxatives. The clip was directed by Sophie Muller, who's known for her collaborations with Gwen Stefani, Shakira, Beyonce, and others.
• "Smile" was a huge hit in Allen's native UK, going to #1 for two weeks. She topped the chart again two years later with "The Fear."
  
  In America, "Smile" stalled at #49, the highest chart position she would ever get to there. Allen sings with a strong British accent, which plays a lot better in the UK.