Rock Docs Podcast: I Am Trying to Break Your Heart: A Film About Wilco, featuring guest Holden Seidlitz

The Rock Docs team is back with yet another entry in the Sam Jones documentary canon. After recently interviewing Jones about his new film on singer/songwriter Jason Isbell, and then a separate episode about that very film, Andy Keatts and David Lizerbram are revisiting Jones’ 2002 documentary, I Am Trying to Break Your Heart. The film follows Wilco during the creation of their acclaimed album Yankee Hotel Foxtrot, which was released that same year, as well as capturing the increasingly fractured relationship between frontman Jeff Tweedy and his then-bandmate, multi-instrumentalist Jay Bennett. Likewise, it delves into the story behind how the album was famously rejected by their label, Reprise, which became an oft-repeated tale—albeit a true one—told about the album.

This week’s guest on Rock Docs is Holden Seidlitz, writer for the New Yorker, and whose work has appeared in Pitchfork, Stereogum, Brooklyn Vegan, and LitHub. Last year, as Wilco released their 2xLP Cruel Country, he took Jeff Tweedy hat shopping.

I Am Trying to Break Your Heart isn’t currently streaming on major providers, but maybe Andy or David will let you borrow one of their DVD copies. In the meantime, hear the new Rock Docs episode and check out the trailer for the film below.