Bachelor No. 2 or, the Last Remains of the Dodo

After Whatever and I'm with Stupid, Mann was seen as someone whose career was in decline. She wrote Bachelor No. 2 in the same period as the Magnolia songs, with Brion collaborating, and said in 2020 that it was the only record for which she took responsibility for all the music, every part played and the way everything sounded. The dodo of the title reflected her sense that singer-songwriters were a dying breed. Many songs came from her frustration with Geffen, whose staff complained that they did not sound like commercial singles. Nothing Is Good Enough was her answer to that criticism. The Fall of the World's Own Optimist was co-written with Elvis Costello, who, she said, fixed a song she could not finish.

Geffen refused to release it. According to Mann, label head Jimmy Iovine asked whether she expected them to put it out as it was. She sold homemade EPs on tour, formed SuperEgo with Michael Hausman, and bought the masters with Magnolia royalties. She sold 25,000 copies by mail order, and after a distribution deal the album passed 270,000. Metacritic gives it 89 out of 100. In The New Yorker in 2000, Nick Hornby called it her strongest work to date and praised its sinuous, Burt Bacharach-like melodies. Pitchfork's Judy Berman, reviewing it in 2019, placed its creation in the Largo scene around Jon Brion.