His father, a television executive, relocated the family frequently as his career developed, and Stringfellow went to elementary schools in New York, Chicago, and Detroit.

In high school, Stringfellow, who had learned to play piano at nine and guitar at 11, met Jon Auer, with whom he would later form The Posies.

In 1988, Stringfellow and Auer began playing together as The Posies and self-released their first album, Failure, which included some of the earlier material they'd written separately.

[5] Failure was well received by the press and put into regular rotation at college and commercial radio stations, prompting Stringfellow and Auer to quickly assemble a full band.

Adding Mike Musberger on drums and Rick Roberts on bass, the Posies made their live debut in May 1988, two weeks after the release of Failure.

Following a series of dates with The Replacements, Hoodoo Gurus, and They Might Be Giants, among others, the Posies were signed by DGC, a Geffen Records imprint.

Dear 23 was released on DGC in September 1990, with the album's lead single "Golden Blunders" appearing in the Top 10 on the college radio charts.

Jon Auer and drummer Frankie Siragusa told radio station KUOW that they had left the band in August 2021 as they learned of allegations from 3 former girlfriends (Holly Munoz Nixon, Kristine Chambers, and Kristi Houk) that Stringfellow had been abusive.

[12] Although the Posies were Stringfellow's main project during much of the 1980s and 1990s, he also performed and recorded with Sky Cries Mary (a band he founded with Auer in 1989), Lagwagon, Saltine, White Flag, and The Minus Five.

Stringfellow co-wrote and recorded several songs with Scott Miller's band The Loud Family in the mid-1990s, appearing as a guest guitarist and vocalist on their albums The Tape of Only Linda (1994) and Interbabe Concern (1996).

[16] The Boston Globe commented that it was a " fascinating left-field listen" noting "the gorgeous back-and-forth dueting of Stringfellow and Munoz".

Released on Lojinx (Europe), Spark & Shine (US) and Target Earth (Japan), Danzig in the Moonlight featured Charity Rose Thielen and Margaret Cho.

It simply is not who I am as a person who respects women.Jon Auer from The Posies quit the band in August after speaking for nine hours with Kristine Chambers, who had made allegations and informed Stringfellow that he no longer planned to work with him.

[8] Following the publication of the allegations, Jody Stephens, lone surviving member of Big Star, published a statement and removed Stringfellow from forthcoming tribute performances.