Songfacts®:

• "The District Sleeps Alone Tonight" explores the layers of anguish Postal Service frontman Ben Gibbard felt following a painful breakup with his first "adult girlfriend." They lived together in Seattle when he was in his early 20s; when they broke up, she moved to Washington, DC, where he met up with her when his other band, Death Cab For Cutie, came through on tour.
  
  "It was just very odd to see this person in this new life that you had no context for," he told Life Of The Record. "What a disconcerting feeling that was for me."
• The "District" in the title is Washington, DC - the District of Columbia - where Ben Gibbard's ex had built her new life and he was merely a visiting stranger. In the song, you can hear Gibbard spiral into a swirl of melancholy as he walks those streets and has a revelation: he was the one worth leaving.
• "The District Sleeps Alone Tonight" was proof of concept for The Postal Service, the duo of Ben Gibbard and Jimmy Tamborello. They were conceived as a correspondence band, mailing each other music and vocals on CDs that they would very slowly craft into songs (thus the band name). It wasn't even their idea - an executive at Sub Pop Records asked them to give it a try after hearing a song by Tamborello's project Dntel with vocals from Gibbard. "The District Sleeps Alone Tonight" was the first song they compiled together; everyone was happy with it, so the full album - Give Up - was a go.
  
  They made nine more songs this way, including "Such Great Heights" and "We Will Become Silhouettes." They did some touring when it was released in 2003 but quickly moved on to other projects - Give Up ended up being their only album. Sub Pop took a low-key approach to promoting it, letting the internet do its thing. The album eventually sold over a million copies, making it one of just two Sub Pop albums to do so - the other is Bleach by Nirvana.
  
  The band reunited to tour for both the 10th (2013) and 20th (2023) anniversaries of the album.
• Tamborello is the beatmaker/producer in the group. He hit on a dreamy electronic sound inspired by Bjork that suited Gibbard's understated delivery very well. This sound ended up with the label "indie pop," which was also applied to the likes of MGMT, Frou Frou and Sylvan Esso.
• That's Jenny Lewis on backing vocals. Her band Rilo Kiley was active at the time and signed to the same label as Death Cab For Cutie, so Ben Gibbard was able to wrangle her into the project. She ended up singing on six songs from the album and also touring with the group.
• "The District Sleeps Alone Tonight" was the second single from The Postal Service, following "Such Great Heights." Sub Pop made a video to promote it, which has a very dreamlike feel as Gibbard seems to be a ghost visiting his ex while she sleeps.
• The British singer Birdy released a piano-heavy cover in 2011. Sylvan Esso put out a remix of the track released by Sub Pop as part of the 20th anniversary campaign in 2023.