With the release of his mammoth Triplicate album last week, Bob Dylan upped the number of Great American Songbook standards he’s covered to 52: 10 on 2015’s Shadows in the Night, 12 on last year’s Fallen Angels, 30 (30!) on Triplicate.

The original idea was that these would all be covers of songs Frank Sinatra once sang. Though Bob’s veered away from that some, Ol’ Blue Eyes still looms large. At their best, these songs embody Sinatra’s emotion and versatility as Dylan finds his own way in to a song. At their worse, they sound like Tony Bennett karaoke by someone who can’t sing.

So with so many of Dylan’s standards covers now out, we decided to rank all 52 songs. Some of Dylan’s finest-ever vocal performances are on these three albums. Also some that make Self Portrait look inspired. So let’s try to separate the wheat from the chaff, the curds from the whey, the In the Wee Small Hours of the Morning from the Sinatra Sings Great Songs from Great Britain.

The Duds:

52. “I Guess I’ll Have to Change My Plans” (Triplicate 1: ‘Til the Sun Goes Down)

When Dylan announced his third consecutive covers album, we titled our post “Bob, Quit It With the Covers Albums.” And when track number one began playing on the latest album, boy did we think we were right. In true obstinate fashion, he kicks off his 30-song set with not only the worst song of this album, but his worst standards cover period. In theory, the addition of prominent horns to Triplicate should help differentiate it from its sometimes sleepy predecessors – and elsewhere it works. But “I Guess I’ll Have to Change My Plans” hints at the nightmare scenario many worried about when Dylan announced he’d be singing standards: a swingin’ Sinatra groove chased by an old man who can’t remotely keep up.

51. “Polka Dots and Moonbeams” (Fallen Angels)

Fallen Angels is the worst of the Dylan covers albums – and that’s even if you separate the three discs of Triplicate (as Bob suggests you do). We named Shadows in the Night the best cover album of 2015. Fallen Angels didn’t even make last year’s list. It supposedly contained cobbled-together outtakes from the Shadows sessions, and it shows, a bunch of songs that are often boring and occasionally horrendous. “Polka Dots and Moonbeams” is in the latter category. Bob straining to hold that high note on “As we floated over the floooor” makes for truly painful listening.

50. “Where Is the One” (Triplicate 2: Devil Dolls)

Let’s not get too bogged down on our journey to the gems. You can click the links if you want to hear the other songs in this category on YouTube or Spotify (where available). Though I wouldn’t recommend it…

49. “How Deep Is the Ocean” (Triplicate 2: Devil Dolls)

48. “Some Enchanted Evening” (Shadows in the Night)

47. “When the World Was Young” (Triplicate 3: Comin’ Home Late)

46. “That Old Black Magic” (Fallen Angels)

45. “It Gets Lonely Early” (Triplicate 1: ‘Til the Sun Goes Down)

44. “Once Upon a Time” (Triplicate 1: ‘Til the Sun Goes Down)

43. “Here’s That Rainy Day” (Triplicate 2: Devil Dolls)

42. “On a Little Street in Singapore” (Fallen Angels)

41. “Somewhere Along the Way” (Triplicate 3: Comin’ Home Late)

40. “It Had to Be You” (Fallen Angels)

The Mediocre Middle:

39. “Imagination” (Triplicate 2: Devil Dolls)

This group of songs are all fine. There’s really not much more you can say about them than that. They’re not embarrassing, Dylan sings passably, the arrangements are pretty enough. Heard individually, one of these might even impress you. But in the context of their respective albums, they quick fade into the pleasant-but-forgettable background.

38. “These Foolish Things” (Triplicate 3: Comin’ Home Late)

37. “Come Rain or Come Shine” (Fallen Angels)

36. “Stardust” (Triplicate 3: Comin’ Home Late)

35. “This Nearly Was Mine” (Triplicate 1: ‘Til the Sun Goes Down)

34. “Autumn Leaves” (Shadows in the Night)

33. “The Best Is Yet to Come” (Triplicate 2: Devil Dolls)

32. “You Go to My Head” (Triplicate 3: Comin’ Home Late)

31. “All the Way” (Fallen Angels)

30. “As Time Goes By” (Triplicate 2: Devil Dolls)

29. “Full Moon and Empty Arms” (Shadows in the Night)

28. “What’ll I Do” (Shadows in the Night)

27. “Young at Heart” (Fallen Angels)

26. “Stormy Weather” (Triplicate 1: ‘Til the Sun Goes Down)

25. “Maybe You’ll Be There” (Fallen Angels)

24. “But Beautiful” (Triplicate 2: Devil Dolls)

23. “Sentimental Journey” (Triplicate 3: Comin’ Home Late)

The Very Good:

22. “Where Are You?” (Shadows in the Night)

Now we’re talking! The fact that almost half of the songs across these five discs are very-good-to-great is, if not quite matching the ratio of his best periods, better than the crooner-Dylan phase of his career often gets credit for. Shadows in the Night was a revelation to so many not because it proved he could sing – anyone who has paid attention to his live shows over the years knows that – but because it showed he could sing on the great singers’ terms. “Where Are You?” is a prime example, Dylan’s passion bringing out a tenderness and care of phrasing not always seen in his own recent work.

21. “I Couldn’t Sleep a Wink Last Night” (Triplicate 3: Comin’ Home Late)

20. “Why Was I Born” (Triplicate 3: Comin’ Home Late)

19. “Nevertheless” (Fallen Angels)

18. “Trade Winds” (Triplicate 1: ‘Til the Sun Goes Down)

17. “All or Nothing At All” (Fallen Angels)

16. “There’s a Flaw in My Flue” (Triplicate 2: Devil Dolls)

15. “Skylark” (Fallen Angels)

14. “That Old Feeling” (Triplicate 1: ‘Til the Sun Goes Down)

13. “The Night We Called It a Day” (Shadows in the Night)

This is the only song on any of the albums to get a music video, but boy is it a doozy. One of Dylan’s best-ever music videos (admittedly not the highest of bars), it’s a violent and wonderful film noir. Dylan couldn’t guarantee that Quentin Tarantino would pick this song for one of his soundtracks, so he made the movie himself.



12. “Why Try to Change Me Now” (Shadows in the Night)

11. “I Could Have Told You” (Triplicate 1: ‘Til the Sun Goes Down)

The Top Ten:

10. “It’s Funny to Everyone But Me” (Triplicate 3: Comin’ Home Late)

Many of Dylan’s best standards deliver deliberate, careful line readings. But “It’s Funny to Everyone But Me” – and a few others in the top ten – succeeds because he lets his hair down a little.



9. “My One and Only Love” (Triplicate 1: ‘Til the Sun Goes Down)

The secret weapon on these albums – and on Triplicate in particular – is Dylan’s longtime bassist Tony Garnier. Whenever a song opens with Garnier’s slow, low bass-bowing, you know it’s going to be a beauty. On “My One and Only Love,” Dylan attempts one of the most vocally challenging songs of the bunch – right in the first line there’s a jump that would foil many trained singers. He nails it.



8. “Day In, Day Out” (Triplicate 3: Comin’ Home Late)

On song #52 – the worst of the bunch – we complained that the horn arrangement hemmed Bob in, forcing him to chase a vocal he couldn’t catch. This horn-driven song is the opposite, an upbeat and joyous number that lets Dylan loosen up. For all his love of Swingin’ Sinatra, Dylan doesn’t actually swing often on these albums. Here he does.

7. “Melancholy Mood” (Fallen Angels)

One of the few true standouts from Fallen Angels (and the only song on that album to make our top ten), “Melancholy Mood” rides a slow drum shuffle to deliver a Bob vocal that underplays the emotion perfectly.



6. “P.S. I Love You” (Triplicate 2: Devil Dolls)

No, this is not the Beatles song – though judging by Bob’s recent “Something” and “Things We Said Today” covers, he’d probably nail that too. Rather, this is an old 1930s Johnny Mercer tune covered over the years by everyone from Bing Crosby to Diana Krall. Dylan finds the romance in this song, bringing to life Mercer’s wonderful workaday lyrics of letter to a spouse: “Write to the Browns just as soon as you’re able / They came around to call / I burned a hole in the dining room table / And let me see, I guess that’s all.”

5. “I’m a Fool to Want You” (Shadows in the Night)

The first song on the first album. For many, the first song they would hear of all 52. It set a terrific template, though also a bar he would rarely again reach. Spare and haunted, it’s a gorgeous vocal that few at that point would have imagined Dylan capable of.



4. “Braggin'” (Triplicate 2: Devil Dolls)

Dylan cares about these songs deeply, working hard to do them justice. One flaw in this focus – especially when you listen to five discs’ worth in one sitting – is there are a lot of slow and somber ballads. So “Braggin'” comes as a breath of fresh air in the midst of Triplicate, an upbeat and goofy number that finds Bob having a blast. It’s a lyric about as profound as his own “Country Pie,” and he has just as good a time singing it.

3. “Stay With Me” (Shadows in the Night)

“Stay With Me” was the first taste anyone had from this American-songbook phase when in October 2014, Dylan began ending his concerts with it, three months before Shadows in the Night came out. I attended one of those fall shows, and was blown away by his performance of it that night. For the many of us who weren’t sure what to expect when he announced a Frank Sinatra covers album, hearing him deliver a careful and impassioned version of this beautiful 1966 Lorraine Ellison was a sign that, as usual, he knew what he was doing.



2. “September of My Years” (Triplicate 1: ‘Til the Sun Goes Down)

It’s easy to read personal biography into a 75-year old Bob Dylan singing a song called “September of My Years.” That said, when you cover 52 songs, one or two are bound to address death. And remember, he was singing “In My Time of Dying” when he was 21. So forget the meta-textual analysis and focus on the beautiful delivery. Accompanied by little more than some steel guitar and Garnier’s bass (there it is again), Dylan delivers one of his best-ever vocal performances.

1. “That Lucky Old Sun” (Shadows in the Night)

Perhaps it’s no surprise that this song is the best of them all, since he’s been practicing it for 30 years. Dylan’s first cover of this song came in 1985, at the first-ever Farm Aid. It appeared again live in 1991, 1992, 1995, and 2000 – never for more than a show or two, but always welcome. Dylan has clearly lived with this song for years now, and every bit of that experience went into the recording. When he strains for – and just barely hits – that climactic high note, it’s one of the most moving movements of his entire recorded career.



These songs are not all on YouTube or Spotify, so you’ll have to head to Amazon to hear them all: ‘Triplicate’, ‘Fallen Angels,’ and ‘Shadows in the Night.’

PS. Here are the power-rankings of the five albums, judged by averaging our individual song rankings:

#1: Shadows in the Night

#2: Triplicate Disc 1: ‘Til the Sun Goes Down

#3: Triplicate Disc 3: Comin’ Home Late

#4: Triplicate Disc 2: Devil Dolls

#5: Fallen Angels

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