Whichever other albums you choose, you must buy Blood On The Tracks (original version, not the bootleg).
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Any three would be good or interesting! But three from different phases, as probably mentioned in one configuration or another above, my three would be:
Love and Theft - latter period, though actually over twenty years old now.
Highway 61 Revisited - starts and ends with two reasons why he’s so mercurially brilliant.
Slow Train Coming - not exactly a deep dive, but an example, for me, of an album that might not slot into the consensus’ view of great, but is Bob doing what Bob wants to do. Plus some great Mark Knopfler playing, too.
FWIW, I thought the film was pretty lame. It stuck to the hackneyed template for music biopics, cf. Ray Charles, Johnny Cash. It was very safe and careful not to distort the received wisdom of those fabled Early Years.
A far funnier and more allusive film about Bob, which for me made more sense as a portrayal and depiction of him as an artist worth investigating, is Todd Haynes’ I’m Not There. This film made me think, the current one just told me what to think.
Or Scorsese’s documentary No Direction Home, if you want a searing, not wholly sanitised, non-dramatised take. And above all others, at least for one point in time, DA Pennebaker’s without parallel, Don’t Look Back.
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I’m waiting for delivery of the Mono Box from Grooves Land. Never ordered from them before, but most reports were OK and it was much cheaper than Amazon.com.
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Hi jegreenwood, I think you may want to check out their feedback first, I was going to order the same box set as you after reading this thread but checked review first which don’t paint a very good picture I’m afraid, I ended up using Chalkys at £77.98.
Live At Budokhan doesn’t strike me as a “way in”, which is what was requested. Some harsh/poor versions of an admittedly wide spread of material but heard in an entirely inappropriate context/terrible venue. If that was my first Dylan purchase it would likely be my last along with any of the religious period, which only really makes sense via the Bootleg series. If you had to have a way in via a live album it would surely be the Bootleg Series summary of the Rolling Thunder tour, which was accompanied by the magnificent Netflix record of that tour.
The Mono Box set is excellent but given that the request was for 3 to 5 which were representative I don’t see how thst works either.
Matter of time before someone suggests Self-Portrait and in seriousness too. There is always one…
I did check the feedback, but I take into account that the number of complaints does not always reflect the percentage of unhappy customers, most of whom have no reason to respond. In any event my package shipped on the 1st.
Freewheelin’ Bob Dylan, Highway 61 Revisited, Blood on the Tracks
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Essential Zimmerman:
-Highway 61 Revisited
-Blood on Tracks
-Desire
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OK @Mandrake, what’s it to be?
For what it’s worth, these are the most-picked (including @Tony’s post at #28):
Blood On The Tracks (9 picks)
Highway 61 Revisited (7)
Blonde On Blone (5)
with Time Out Of Mind & Freewheelin’ joint fourth.
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Highway 61 and Blonde on Blonde were from the same era. Both are great, but somewhat redundant from an overview perspective.
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Well often cited as THE greatest trilogy in modern rock:
Bringing It All Back Home
Highway 61 Revisited
Blonde On Blonde
can’t really be beaten (asides from the two Bowie trilogy’s 
), but they’re all from one era.
A more balanced three for a greater sense of the mans genius would (IMHO) be:
Blonde On Blonde
Blood On The Tracks (his best for me)
Time Out Of Mind (I prefer the later remixed version ‘toning down’ Lanois’ production)
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Those are definitely the first three (for me). Then Blood On The Tracks
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Bringing it all Back Home - because it catches him on the cusp of change between acoustic and electric and shows he can do both. There is a perfection to Side B (the last four songs).
Blood on the Tracks - the apogee of confessional 70s rock. Also some of it is unintentionally hilarious - eg If you see her say hello (‘She might be in Tangiers’ )
The Basement Tapes - because it invented the Americana genre
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I agree Self Portrait is awful, but have you every checked out Another Self Portrait (Bootleg series vol 10)? It’s genuinely very good.
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Oh Mercy a excellent album with superb sound quality.
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Blonde on Blonde
Blood on the Tracks
Desire
These are my top three although I have most of his others with the exception of those released in the last 15 years or so.
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I’ve most of the BS and you’re right. Another Self Portrait was something of a revelation. Just showed the extent to which he would self sabotage.
The one’s I enjoy the most are:
Blood on the Tracks
Slow Train Coming
Oh Mercy
Wasn’t the question
You should also listen to John Barleycorn - Must Die album while you are there