Bob Dylan – Christmas in the Heart | Surprisingly Beautiful, Deeply Sincere Christmas Album
This is the first episode of our relaunched Playback, shifting from a more sketch/comedy video show into a full-on music podcast, and we kicked it off with one of the most unlikely picks: Bob Dylan’s Christmas in the Heart.
On this episode, we talk about how we went in half-expecting a novelty record… and came out honestly loving it. We get into why Dylan is actually the perfect artist to treat this material with total respect, even though the album itself never really got respect from a lot of listeners or critics.
Christmas in the Heart is Dylan’s first and only Christmas album, released October 13, 2009 on Columbia Records. It’s his 34th studio album (47th overall), and it’s a collection of traditional hymns, carols and classic Christmas songs like “Here Comes Santa Claus,” “Do You Hear What I Hear?,” “Winter Wonderland,” “Hark the Herald Angels Sing,” “Little Drummer Boy,” “Have Yourself a Merry Little Christmas,” “Must Be Santa,” and more.([turn0search0turn0search2)
Dylan produced the album himself under his Jack Frost pseudonym, recording in May 2009 at Groove Masters in Santa Monica with members of his touring band plus guests like David Hidalgo and a full choir.([turn0search0turn0search4) All of his royalties from the album are donated in perpetuity to Feeding America in the U.S., Crisis in the UK and the UN World Food Programme — turning this project into a literal charity engine as well as a weird, wonderful entry in his catalog.([turn0search0turn0search11turn0search13)
We talk about:
• How Dylan leans into the old-school crooner/choir Christmas album tradition—Nat King Cole, Ray Conniff, etc.—but filters it through his late-career voice and phrasing ([turn0search13)
• Why the “he’s trolling” narrative doesn’t hold up when you actually listen to how straight he plays these songs, and why that seriousness moved us
• How his decision to donate all royalties reframes the album as an act of generosity and gratitude, not a cynical cash-grab ([turn0search0turn0search11)
• The production choices: arrangements, band feel, the way his voice sits in the mix, and why “Must Be Santa” somehow becomes one of the most chaotic, joyful Christmas tracks ever
• How this album ended up being the perfect subject for our first “new-format” Playback: digging into a record people joke about and discovering something quietly profound
This is very much a cozy, late-night, December episode about tradition, sincerity, aging voices, and the weirdness of Dylan doing a charity Christmas album that might secretly be one of the most honest holiday records ever made.
Chapters:
0:00 (Intro)
6:08 (First Impressions)
19:35 (Bob Dylan is A Great Singer)
33:15 (Standout Songs)
58:13 (Closing Thoughts)
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This episode is for fans of Bob Dylan, Christmas music, misunderstood records, late-career vocal weirdness, and longform album talk that takes “joke albums” seriously.
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