Songfacts®:

• "Sister Tilly" is Natalie Merchant's heartfelt tribute to a certain type of woman from her parents' generation. It includes a shout-out to Joan Didion, the fearless American writer who died during the week Merchant was recording her vocals.
• Merchant wrote "Sister Tilly" after the 1960s model Sally Grossman died during the pandemic. She is best known as the young woman lounging by a fireplace on the cover of Bob Dylan's 1965 album Bringing It All Back Home.
  
  "I'd known her for years and she was always an inspiration... a really strong woman," Merchant told Uncut magazine. "It's also made me think about the fact that so many women of that generation are passing now. I even mentioned Joan Didion in the lyrics, who died while we were making the record. So, it became this tribute to these women that we owe so much too."
• Oh, Miss Tilly, I think you should know everyone's missing you here
  Your fortune telling cards, prayer flags in the yard
  Rilke poems and your stacks of Mother Jones
  Your feminist raves in your Didion shades
  And your Zeppelin so loud, so proud
  Zeppelin so loud, so proud
  Here's to your days at the barricades
  
  Merchant weaves multiple references to the 1960s liberalism throughout the song: from the prevalence of fortune-telling and Tibetan prayer flags to the popularity of the left-wing magazine Mother Jones. The music scene of that era is also nostalgically captured, with iconic bands like Led Zeppelin among the most beloved during the late '60s and early '70s. Additionally, the imagery of barricades evokes memories of the Vietnam War and the women's liberation movements, symbolizing the spirit of protest and social change from that transformative period.
• Following several years of dedicating herself to being a single mother, Merchant returned to songwriting in late 2020 or early 2021, marking the first time in six years since she had written new material. Keep Your Courage takes the form of a song cycle centered around the theme of possessing a courageous heart. It's made up entirely of songs about love in its many forms.