Songfacts®:

• "Heartless" finds The Weeknd talking about his party lifestyle. He presents himself as a "heartless" person who engages in mindless sex and takes plenty of illegal substances. The singer's experiences have hardened him, leading him to shut off his emotions and pursue this soulless existence. The Weeknd is addicted to his way of life and does not expect to change his hedonistic ways.
• During the bridge,The Weeknd addresses someone he says has never given up on him; she's the only one who can help him climb out of his personal hole. There's speculation he's talking to his on-off model girlfriend, Bella Hadid, who he's been involved with intermittently since 2015.
• The Weeknd wrote the song with:
  
  Hip-hop songwriter Dre Moon, who in 2015 won a Grammy Award for Best R&B Song for co-composing Beyonce's "Drunk In Love."
  
  Atlanta-based producer Metro Boomin, who works frequently with Future. He helped craft The Weeknd's collaborations with Future, "Low Life" and "Six Feet Under."
  
  The Weeknd's long-term collaborator, Illangelo. The Canadian producer helmed the entirety of The Weeknd's 2011 trilogy of mixtapes and several of his Beauty Behind The Madness tracks. This is his first song credit on an Abel Tesfaye tune since then.
  
  Metro Boomin, The Weeknd and Illangelo all produced the song.
• The song's trippy music video was shot in Las Vegas and directed by Anton Tammi (Halsey's "Graveyard"). The clip takes The Weeknd to the Strip, where he is joined by his producer and cohort Metro Boomin on a drug-fueled bender. Their gambling, drinking and smoking lines up with the song's lyrics about the Toronto star's hedonistic lifestyle. However, the wild night becomes increasingly blurry and it all catches up with The Weeknd.