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According to Discogs there exist three guys named Winston Watson.
This guy is a drummer and worked in Dylan’s Neverending Tour Band. Real name is supposedly Winston A. Watson Jr. according to Discogs. Roon seems to know him as “Winston Watson”.
According to Discogs, he also worked with Giant Sand, but I am not entirely sure of that - see below.
This guy is a Reggae singer and worked in The Meditations and with Bob Marley as background singer.
Confusingly, Discogs cites a third Winston Watson who is a recording engineer from Tucson, Arizona, who also worked with Giant Sand and Giant Sand’s main man, Howe Gelb. This makes sense because Giant Sand stem from Tucson and worked with many local engineers over their long career. I am not entirely sure whether Giant Sand / Howe Gelb really worked with one Dylan drummer of the name Winston Watson in addition to an engineer who happened to have the same name, or whether in fact the recording engineer actually also played drums with Giant Sand / Howe Gelb, and the Dylan drummer never did:
Now, Roon has one artist that has a Valence picture like the Dylan drummer on Discogs, and it says “Member of” Neverending Tour Band. So I suppose this is correct.
(Note: The Pop/Rock genre was added by me, genres are empty by default)
However in his Discography, it contains also works from the Reggae guy, which seems clearly wrong:
Curiously, the Dylan drummer WW’s avatar does not look like the guy in the landscape picture at all:
(Note that instruments are Vocal Harmony, Background Vocals because this screenshot comes from a Marley or Meditations album)
The Dylan drummer is also credited on Howe Gelb’s Confluence (screenshot shows unedited Tidal version), and on several other Giant Sand / Howe Gelb albums.
At this point it may also be noted that the above screenshot shows one Joe Burns and one Joey Burns on Bass. Only Joey is correct.
The Dylan drummer is also credited on a lot of other albums from Warren Zevon to Chuck Prophet. I have no idea whether these are correct.
One additional interesting detail is that he is credited on Me and the Devil by Chris Cacavas & Edward Abbiah. Cacavas once played in Giant Sand, so might be using the same guy.
In the Associated With section, he is associated with some Reggae luminaries:
In the Recommended Albums, I have no idea what the associations are and which Winston they are based on:
The Reggae Winston Watson which should be credited on the works as a Reggae vocalist does not exist in Roon at all, which seems clearly a mistake. Albums on Qobuz by The Meditations or Marley have credits for the Dylan drummer.
It gets stranger:
Roon does know another artist named Winston A. Watson Jr. Recall that Discogs says that this is the real name of the Dylan drummer.
This Winston A. Watson Jr., however, is credited on Ballad of a Thin Line Man by Giant Sand. (screenshot shows unedited Tidal album)
As confusing as it is, the following issues can probably be identified and are fixable on a logical level:
- The Reggae singer should exist and be credited to the Meditations, Marley, etc.
- The Dylan drummer should not be credited on the Meditations, Marley, etc.
The following might require more information about the artists before it can be fixed:
- Is the Dylan drummer’s real name really Winston A. Watson Jr.? If yes, the separate artist Winston A. Watson Jr. should be merged with the Dylan drummer Winston Watson.
- Did the Giant Sand / Howe Gelb engineer play drums on the Giant Sand / Howe Gelb as well? In this case, he should exist in Roon and be credited appropriately, and the Dylan drummer’s credits should be removed.
- If the Dylan drummer did really play with Giant Sand / Howe Gelb and is separate from the engineer, all three Winston Watsons should exist in Roon, but it would be nice if they were differentiated by avatars, which should exist at least for the Dylan drummer and the Reggae singer.
I might have to bother him and ask Howe Gelb the next time he plays in Berlin.
It seems the same on AllMusic as it is in Roon. It finds the mix of Dylan drummer and reggae singer, and the Winston A. Watson Jr:
The Dylan drummer with the same pic as in the Roon avatar, but tagged with genre Reggae and having Dylan, Marley, and Giant Sand in the credits:
The A. Junior with two Giant Sand credits on drums:
On Tidal, “Winston Watson” has the same pic as AllMusic and the Roon avatar, and in the credits also has Dylan, Marley, Meditations, and others that I don’t know. However, it does not have him associated with Giant Sand or Howe Gelb. There is also an additional songwriter Winston Augustus WATSON that has no associations with anything.
On Qobuz, there is one Wintson Watson, associated with just one album as primary artist, Born to Sing. It is tagged as (and is) Reggae from 2017. This same album is also associated with the Winston Watson on Tidal and in Roon
Have you made any edits to this content in Roon?
I did make some edits to the Marley, Giant Sand, and Howe Gelb albums in the past, and also the artists, but I did do my best to make the screenshots all show unedited versions. So if I didn’t make a mistake, you should be able to reproduce it. I also tried to make sure that screenshots only show versions from online streaming (I have many local ones for Giant Sand / Howe Gelb)
Is the album identified in Roon?
All screenshotted albums are identified
Is this content from local files, TIDAL, or Qobuz?
I tried to do all screenshot from Tidal. Spot checked the Qobuz equivalents as well and they were the same. My local albums of Giant Sand and Howe Gelb are similar, where they received Winston Watson credits from Roon.
There is clearly good evidence that the Dylan drummer (Winston Watson 
