Helplessly Hoping

Stills first recorded it as a demo in 1968, released in 2007 on Just Roll Tape. The trio cut it at Wally Heider's Studio 3 in Hollywood in December 1968, their first recording session as a group, with Paul Rothchild producing. Atlantic released it on the debut album on 29 May 1969, and it was the B-side of Marrakesh Express.

Stills wrote the song for Judy Collins, about his struggles after their break-up. The lyric leans on alliteration and wordplay, and the numbers in the chorus carry a second meaning that the harmonies echo: every new line adds an extra voice. Stills sang lead and played acoustic guitar, with Crosby and Nash singing lead and harmony.

A live version recorded at the Fillmore East on 20 September 1969 was released in 2024 as a preview of Live at Fillmore East, 1969. The song has been covered by J. D. Crowe and the New South (1986), Taxiride (1999), Foxes and Fossils (2013), Home Free (2017) and Of Mice & Men (2021), and Richie Havens also recorded it. It turns up in the 2018 film Annihilation and in the video game The Last of Us Part II.