Needles & Grooves

The mono Box obviously

Agree BOTT....other two some mix of Hwy61, Blonde on Blonde, or Bringing It All Back Home

@Crabbers technically has the best answer and then you can still get 2 more

If I were to get only three, Freewheelin' is the best of the first four (the acoustic records), and then Highway 61 or Blonde on Blonde, and Blood on the Tracks. But I have a feeling you'll get more eventually. Highway 61 and Bringing It All Back Home were my entry points.

He has a number of essentials.

For starters
Blood On The Tracks
Highway 61 Revisited
Blonde On Blonde
Bringing It All Back Home

Maybe in that order

Moving on
The Bootleg Series 1-3 (A compilation of outtakes but rare quality)
The Freewheelin
Desire
Street Legal
Time Out Of Mind
Love & Theft
I could go on...

related: is this the real price of the mono box set? seems very low unless they pressed like thousands of them - https://www.amazon.com/Original-Mono-Recordings-Vinyl/dp/B003ZYJS5Q

There is no way you can do it in three sorry, the man has 40 Something albums and at least a quarter of those are defining pieces in popular music. If you really want to be casual get the 3CD Dylan compilation box, but you’ll be missing tonnes of good stuff even still.

In terms of his absolute best albums (and I’m still cutting ones I consider great out here)

The Freewheeling Bob Dylan
Bringing It All Back Home
Highway 61 Revisited
Blonde on Blonde
Nashville Skyline
Planet Waves
Blood On The Tracks
Desire
Street Legal
Time Out Of Mind
Love & Theft
Modern Times
Tempest

@wokeupnew hasn't this low price been the buzz of here for a few months now? Everyone seems to be on it! I’d imagine amazon are clearing old stock given its original release date.

Yep that’s the box @wokeupnew

I'm extremely tempted that's like $15~ and LP. I think I may need to do it. I've been looking in used shops for Dylan's but they're always way overpriced.

@Joe Mac @wokeupnew I think the box was re-pressed, since the download code no longer has an expiry date like the 2010 (?) run did. Some are numbered and some aren't.

Hey I jumped into Dylan with this box...I’m very pleased with it...plus your box might be numbered

@wokeupnew if you don’t have any and want them, and even if you have one or two overlapping, jump on it. These albums are best in mono and the reports on here of the pressings are very positive. I’d have been all over it if I hadn’t already got all 8 in mono...

I’m going to be controversial here and say if you only want 3 don’t go near Blonde on Blonde. It’s highs are great but it’s a bit inconsistent and it’s probably 6th or 7th in my Dylan list...

@Joe Mac Rainy Day Women is terrible // I only have Freewheelin', not sure if it's mono, probably stereo. I don't mind having multiple copies with that one.

I think Rainy Day Women is by far the worst song on the record but it's a fun little starter. But I'd agree, it's not in his top three albums.

@Joe Mac I tend to agree. Blonde on Blonde is rather sprawling. It does have some classic tunes on it though. I think of that three album run, Bringing It All Back Home is kind of the sleeper. I like the half acoustic/half electric split, and it has some of my favorite album tracks on it.

@Aron Bringing It All Back Home is my favourite of that trio! Highway 61 Revisited is pretty much at the same level. I mean I’m not knocking Blonde on Blonde it’s still brilliant. Sad Eyed Lady Of The Lowlands

I didn’t get the box as my copies of all of those albums bar Bob Dylan and Freewheelin are mono versions. If you have nothing it’s worth jumping into the box. Street Legal is a personal favourite.