Three tracks on the album - "No More A-Roving," "The Letters" and "There For You" - came from the Ten New Songs recording sessions, Cohen's previous album from 2001. As such, Sharon Robinson supplied the music, production, and singing for these songs. The rest of the material came from various sources that feature Cohen experimenting with different musical approaches. On "To a Teacher," Cohen quotes himself from The Spice-Box of Earth, his second collection of poetry from 1961. The basic tracks of "The Faith" dated back to the Recent Songs sessions from 1979. The album concludes with a live version of the country standard "Tennessee Waltz," which was taken from a performance during his tour in support of the LP Various Positions. Considering the plethora of sources from which the material sprang, Cohen had originally wanted to call the album Old Ideas, but eventually changed it to Dear Heather for fear that fans might assume it was merely a compilation or "best of" package (Old Ideas would be the title of Cohen's next studio album). There is a marked increase in spoken poetry over singing, with two songs featuring words by other writers: Lord Byron ("No More A-Roving") and F.R. Scott ("Villanelle for our Time"). The gospel-tinged "On That Day" addresses the still-raw tragedy and horror of the 9/11 terrorist attacks.
Cohen did not tour or do interviews to support the album, which was dedicated to Cohen's ailing friend Irving Layton, the late Canadian poet A.M. Klein and the late R&B singer Carl Anderson.
The album reached #131 on the Billboard 200 and Internet Album charts and #5 on the Canadian Album charts. It was Cohen's highest charting album in America since 1969's Songs from a Room. The album's highest chart position came in Poland where it reached #1 on the Polish Albums ChartDear Heather was not received as well by critics as Ten New Songs and Cohen's 2001 live album Field Commander Cohen: Tour of 1979 had been. Some critics found it dour - although such notices had been commonplace throughout various stages of Cohen's career - and noted a tone of finality in the offering. The New York Times reported, "Some of the songs are virtually unadorned with poetic imagery and fall flat; in others, Mr. Cohen uses his calmly sepulchral voice for speech rather than melody. The production is homemade." The Stylus deemed it an "unsatisfying way to end such an intriguing career." In the November 2004 Rolling Stone review of the LP, Michaelangelo Matos praised the album, calling Cohen "Canada's hippest 70 year old" and insisting that "given how monochromatic Cohen tends to be, the jumbled feel works in Dear Heather's favor." Thom Jurek of AllMusic argues that Dear Heather is Cohen's "most upbeat" album: "Rather than focus on loss as an end, it looks upon experience as something to be accepted as a portal to wisdom and gratitude...If this is indeed his final offering as a songwriter, it is a fine, decent, and moving way to close this chapter of the book of his life."
Tracks 1, 3 and 8 were produced by Sharon Robinson. Tracks 2, 4–5, 7, 9 and 11 were produced by Leanne Ungar. Track 6 was produced by Anjani Thomas. Track 10 was produced by Anjani Thomas and Ed Sanders. Track 12 was produced by Leanne Ungar and Henry Lewy. Track 13 was produced by Leonard Cohen in 1985.
"Go No More A-Roving" is musical adaptation of Lord Byron's poem "So, we'll go no more a roving", dedicated to Cohen's friend and mentor, Canadian poet Irving Layton, member of the Montreal Group of modernist poets.
"Villanelle for Our Time" was recorded 6 May 1999, shortly after Cohen's return from Mount Baldy Zen Center. It is an improvised jazz recitation of a poem by F.R. Scott, Cohen's older colleague from the Montreal Group of modernist poets.
The track "Nightingale" is dedicated to the late R&B singer Carl Anderson, Anjani Thomas's colleague. She composed the music using Cohen's abandoned poem.
Music track for "The Faith" is actually an outtake from Recent Songs, with completely new lyrics, re-mixed and with new vocals added (thus the production was co-credited to Recent Songs producer Henry Lewy).
The final track is a live performance of "Tennessee Waltz", recorded 9 July 1985 at the Montreux Jazz Festival. It was taken from the bootlegged radio recording and cleaned up digitally.