The second single from Ed Askew‘s posthumous album The Final Painting is out today. Tough Guys is a slow, bittersweet chamber-pop piece — a song about gay relationships Askew both observed and lived, set against a backdrop of handsome boys and former flames circa 1980.
The Final Painting arrives on July 31st via Drag City, assembled in the last years of Askew’s life with producer Jerry David DeCicca, who worked with Ed on 2013’s For the World. As we reported in May, DeCicca received nearly three dozen songs from Askew in various stages of completion before the pair expanded nine of them into what amounts to a stunning final self-portrait.
Where lead single Gray Air-o-Plane — featuring Sharon Van Etten — opened the album with the weathered intimacy of an old poet taking stock, Tough Guys moves differently. Between Ed’s piano and vocals, the arrangement fills with the episodic feel of soundtrack music and the languid ease of ’70s chamber pop. Trumpet from Fulvio Sigurta blows smoothly through the piece, and the song builds slowly, the emotional temperature rising almost imperceptibly. Ed’s lyrics are crushingly direct: “They left like a lover / they left like a mystery / they left and they kissed me.”
To coincide with the album’s release, an exhibition of paintings from Askew’s final working years — Boy with a Hat: Ed Askew, Paintings 2014–2024 — opens at the Soccer Club Club venue in Chicago on July 31st and runs through August 21st. Curated by Jay Pluck, Askew’s longtime friend and collaborator, the show includes the painting Askew himself chose for The Final Painting‘s album cover, believed to be the last work he completed. The opening reception on Friday, July 31st (8–11PM, refreshments by Middle Brow) will feature a live performance from album contributors Eve Searls, Dustin Laurenzi, and Jerry David DeCicca.
The Final Painting (July 31st, 2026) Drag City
Pre-order: lnk.to/finalpainting