Songfacts®:

• "When I Wake Up" finds Taylor Momsen looking back on a period in her life when partying stopped being an escape and became a trap. Driven by a mix of blues-rock and punk, she chronicles nights of sex, drugs and reckless abandon that end in mornings clouded by confusion, where Momson barely knows where she's woken up, or who she's beside. Although the singer repeatedly suggests everything is fine, she's clearly living in a cycle that's unsustainable.
  
  "'When I Wake Up' is the story of a dream becoming a nightmare," said Momson. "When a life of excess leads you on a rollercoaster that is doomed to crash but you just can't see it."
• The song draws directly from Momson's own experience of living what appeared to be a glamorous rock-and-roll lifestyle that had become unsustainable.
  
  "The song's actually quite dark," Momson told NME. "I'm proud of it because on a first listen, if you're not paying much attention, it's a very fun song. It's meant to be like that. It mirrors a time period in my life where I was in the fast lane and from the outside it looked like a really good time. But if you look slightly under the surface, the reality is that's not a sustainable life, where at some point you have to wake up from that and make a choice."
  
  Momsen eventually reached a point where she had to decide whether she wanted to live or die. "I was in a very bad place. That song is reflecting on that time period where I was very out of control... I was trying to use things outside of myself in order to escape my own brain and the circumstances that I felt like I was trapped inside of. I chose the unhealthy way to go about things for a while."
• Momsen wrote "When I Wake Up" with The Pretty Reckless guitarist Ben Phillips. The pair also co-produced the track with Jonathan Wyman, who became the band's producer following the death of longtime collaborator Kato Khandwala in a 2018 motorcycle accident.
• The NSFW music video, co-directed by Momsen and Chris Acosta, translates the song's themes into a chaotic point-of-view journey through one increasingly destructive night. Packed with sex, drugs and rock-and-roll imagery, the clip stars Momsen alongside several familiar faces, including her former Gossip Girl castmates Jessica Szohr and Connor Paolo, and Foo Fighters members Pat Smear and Ilan Rubin.
  
  "I wanted the video to reflect where the song came from – a time in my life when I was out of control, not caring whether I lived or died. We shot it raw, with no grade, no filter," Momson told Kerrang!. "Reality doesn't come color-corrected, and I didn't want to change what we captured. The imperfection is the grade."
  
  Regarding the video, Momson said it illustrates "where life can take you when you play too close to the edge," describing it as a portrait of chasing "substances, sex and dopamine highs to escape depression," only to discover that the pursuit leaves a person emptier than when they began. It is, in other words, a cautionary tale delivered with enough volume to rattle the windows.
• Released as one of the lead singles from The Pretty Reckless' fifth album, Dear God, "When I Wake Up" introduces many of the record's central themes: self-destruction, existential struggle and the difficult search for redemption after hitting rock bottom.