The 75-year-old music legend was close to the heavyweight great Ali, fellow singer/songwriter Cohen and deceased musicians Leon Russell and Merle Haggard, all of whom passed away in 2016.
Dylan admits those men were like ''brothers'' to him and the loss of all of them has hit him hard.
In an interview with author-and-TV executive Bill Flanagan published on his website BobDylan.com, he said: ''They all [hit me hard] - we were like brothers, we lived on the same street and they all left empty spaces where they used to stand. It's lonesome without them.''
When asked to consider the greatness of some of his fallen friends and peers, the 'Forever Young' songwriter mused: ''I can't say who's great or who isn't. If somebody does achieve greatness it's only for a minute and anyone is capable of that. Greatness is beyond your control - I think you get it by chance, but it's only for a short time.''
Although he couldn't call her a friend, Dylan also remembered late British singer Amy Winehouse - who tragically died in 2011 from alcohol poisoning at the age of just 27 - and admitted he respected her as an artist.
As if he was a fan of Winehouse, Dylan said: ''Yeah, absolutely. She was the last real individualist around.''
Dylan also remembered a conversation he had with the late Frank Sinatra in which he told him that they were both from the stars because they had ''blue eyes''.
The 75-year-old musician has recalled a dinner party at the late Sinatra's house, also attended by Bruce Springsteen, and at one point during the course of the evening the 'My Way' crooner took him to one side to tell him that they were different from other ''bums''.
He said: ''He was funny, we were standing out on his patio at night and he said to me, 'You and me, pal, we got blue eyes, we're from up there,' and he pointed to the stars. 'These other bums are from down here,' I remember thinking that he might be right.''
Dylan paid tribute to Sinatra - who died in 1988 at the age of 82 - with
his 2015 album 'Shadows in the Night', which was comprised by traditional pop standards made famous by the late icon.
He released his new album 'Triplicate' on March 31, his third LP of standards following 'Shadows in the Night' and 2016's 'Fallen Angels'.
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