In 2003 Haley's album ...The Size of Planets (Chairkickers Union) received favorable reviews in the Twin Cities press.

She also toured with Mason Jennings, Richard Buckner, Rivulets, and Mary Lou Lord, who was also Haley's manager for a time.

She sang on the feature song "Quiet Breathing" from the independent film Sweet Land, directed by fellow Minnesotan Ali Selim, and collaborated with Actual Wolf and Gary Louris.

Jeremy Ylvisaker (Andrew Bird, Alpha Consumer, Guitar Party), Jacob Hanson (Halloween, Alaska, Guitar Party, Minneapolis Dub Ensemble), Haley Bonar, Luke Anderson (Rogue Valley, Alpha Centauri), and Mike Lewis (Happy Apple, Fat Kid Wednesdays, Andrew Bird, Gayngs) are all members of Gramma's Boyfriend, though the band's website states that "sometimes they all play together, sometimes its whoever shows up.

[17] The album earned widespread critical acclaim, with Stephen Thompson of NPR calling Haley "a bright, subtle storyteller, [who] displays a mastery of pop-rock craftsmanship that keeps these songs as relentlessly catchy on the surface as they are alluringly complex underneath.

"[18] SPIN lauded the track "No Sensitive Man" as "dynamic, demanding,"[19] while Consequence of Sound stated that "Bonar creates a whimsical masterclass of indie-pop songwriting.

[26] Saxophonist Mike Lewis of jazz band Happy Apple guests on the song "Pig Latin."

[29] The album was inspired by Beatrix Potter's The Tale of Two Bad Mice and the murder of George Floyd and subsequent unrest centered in her Twin Cities hometown.