Songfacts®:

• "Dear Insecurity" is Brandy Clark's musical smackdown to those pesky self-doubts that haunt us all. As she sat in the soul-crushing LA traffic on her way to a writing session with Michael Pollack (Maroon 5's "Memories," Miley Cyrus' "Flowers"), the song idea struck her like a bolt of lightning. Clark was thinking about someone who'd wounded her pride, and a friend's blunt reminder that "insecurity is the ugliest human emotion."
  
  "I was thinking, 'It's really insecurity. I need to remember that: They're making me feel bad because they feel small,'" Clark recalled to American Songwriter. "I was sitting there in traffic, and I wanted to bring a really great idea to Michael, and I was like, 'What if you wrote a letter to insecurity?'"
• "Dear Insecurity" is a track from Clark's eponymous fourth studio album, produced by the acclaimed singer-songwriter Brandi Carlile. The pair previously collaborated on Clark's 2020 single "Same Devil."
• Carlile wanted to make "Dear Insecurity" a duet, so she joined Clark on the initial scratch vocal. Clark was so moved by the way their voices intertwined over the raw, heartfelt lyrics that she decided to keep the duet with Carlile.
  
  "She had a couple of people in mind, but Lucinda Williams was top of her list and mine," said Clark to UK newspaper The Sun. "And so, she sang the scratch vocal with the hope of playing it for Lucinda and getting her on it. She even tried to sing it the way she thought Lucinda would. However, she got lost in it as did I, we were in the middle of some magic, and I couldn't imagine anyone BUT Brandi singing it with me. Luckily she agreed."
• "Dear Insecurity" won the Grammy Award for Best Americana Performance. It was the first win for Brandy Clark after 11 nominations, including her Best New Artist nom in 2015 that put her up against Iggy Azalea, Haim, Bastille and the winner, Sam Smith.