First, Cliff Rold's thread examining Hoylfield's career in terms of all time status is a helpful starting point:
http://www.boxingscene.com/measured-against-all-time-evander-holyfield--17642
Now, for my own analysis. In a time period where enough time has elapsed in most divisions that there is some dispute as to who the best of all time in each division is, cruiserweight is the exception. This is because the division has been around for such a short amount, of time, which in turn, also caused almost all of the best fighters of all time in that division fight each other in the late eighties. Holyfield emerged victorious against most of the names that still reside on the best of all time cruiserweight lists.
The Ring's all time rankings of the division, published in 1994 is as follows:
1. Evander Holyfield
2. Dwight Muhammad Qawi
3. Carlos de Leon
4. Ossie Ocasio
5. Orlin Norris
(http://boxrec.com/media/index.php/Division-By-Division_-_The_Greatest_Fighters_of_All-Time)
Cruiserweight title fights
Dwight Muhammad Qawi - SD15 for his first cruiserweight title in the form of the WBA belt.
Henry Tillman - TKO7 win over the 1984 Olympic gold medalist.
Ricky Parkey - TKO3 win over to unify the WBA and IBF belts.
Ossie Ocasio - TKO11 win over former WBA titlist.
Dwight Muhammad Qawi - KO4 win to avenge the close split decision in the first fight.
Carlos de Leon - TKO8 win to become undisputed by unifying the WBA, IBF and WBC belts. De Leon was the current WBA titlist, had previously held the WBA twice before, and won the WBA title after Holyfield left the division.
Obviously his cruiserweight resume speaks for itself. He had one close fight, which he avenged by early round KO in the rematch. He fought everyone he possible could at the weight, and beat all of them beyond a shadow of a doubt. With no other accomplishments possible at the weight, he moved up to heavyweight to chase Mike Tyson's titles. To make the case that he deserved a shot at the heavyweight championship, he rattled off six straight KO wins, against fairly decent decent opposition for non-title fights.
Significant heavyweight fights previous to first title shot
James Tillis - Best known as the first fighter to take Tyson the distance.
Pinklon Thomas - former WBA titlist.
Michael Dokes - former WBA titlist.
Alex Stewart I - undefeated.
These fairly impressive wins, combined with the fact that they were all by KO earned Holyfield his first title shot at heavyweight.
Significant heavyweight fights in his prime (and maybe a little after)
James "Buster" Douglas - Destroyed the out of shape Douglas in three short rounds to become known as the undisputed champion of the division.
"Big" George Foreman - Performed well against a very old Foreman who showed that he had a lot more left to give to the sport than people thought. Holyfield weather big punches and delivered many more big punches of his own in his first fight that went to decision in a little less than five years.
Bert Cooper - Holyfield had to deal with adversity for the first time in the division as he was knocked down for the first time in his career in this fight. He weathered the storm and knocked out Cooper in seven rounds.
Larry Holmes - Bested the much larger, but faded Larry Holmes in a comfortable unanimous decision victory.
Riddick Bowe I - Lost his undisputed championship in the best heavyweight fight since 1990. He showed more heart in this fight than people thought possible, battling back from nearly being out on his feet in round 10 to end up hurting Bowe towards the end of the round.
Riddick Bowe II - Avenged the loss of the first fight against a heavier, out of shape Bowe, in a strange event that involved Fanman. Holyfield recaptured the WBA and IBF titles (the WBC had been vacated when Bowe choose not to fight Lennox Lewis in one of the most obvious ducks in boxing history).
Michael Moorer I - Lost his titles during his time of heart problems and Hepatitis A that significantly affected his ability to fight at his full potential.
Riddick Bowe III - Lost the rubber match to Bowe, which is no largely blamed on his heart problems and Hepatitis A.
Mike Tyson I - Tyson had captured two world titles (WBC through Frank Bruno and WBA through Bruce Seldon) during Holyfield's streak that involved as many wins as losses. Holyfield got the better of Tyson through the whole fight, and ended up knocking him out in the 11th round, recapturing a heavyweight title (in the form of the WBA title) for a third time.
Mike Tyson II - In an extremely strange even that involved Holyfield losing a chunk of his ear to an incident of biting, Holyfield was getting the better of Tyson again early. After a major point deduction, Tyson bit Holyfield again, and caused the referee to award the fight to Holyfield as a disqualification win.
Michael Moorer II - Holyfield avenged his first loss to Moorer by knocking him down five times in a totally dominant victory. He also recaptured the IBF title in this unification match.
Lennox Lewis I - Holyfield was handled fairly easily by Lennox Lewis in a fight that would once again unify the IBF, WBA and WBC titles. However, to the shock of many, the judges scored the fight a draw, keeping the titles from being unified.
Lennox Lewis II - Holyfield fought a much better fight, but ultimately loses a decision in a close fight, making Lewis the undisputed champion of the division.
John Ruiz I - Holyfield wins the vacant WBA title by unanimous decision.
John Ruiz II - In a rematch, Holyfield drops a unanimous decision to lose the WBA title.
John Ruiz III - Ruiz retains his WBA title in the rubber match that ends up being scored a draw by the judges.
This section of Holyfield's career is really what he can hang his hat on to justify his place as an all time great without a shadow of a doubt. He had many wins over fighters who had either established themselves as a relevant fighter in the division or would go on to do something significant after Holyfield fought them. Foreman ended up winning the lineal championship from Michael Moorer after the Holyfield fight. His win over Riddick Bowe still registers as Bowe's only career loss. Tyson was coming off wins over defending titlists Frank Bruno (WBC) and Bruce Seldon (WBA), and he was still a pretty good fighter, even if he wasn't 100% of his excellent prime self. His rematch win over Moorer was significant as he had just beaten Axel Schulze (who had just given Foreman all he could handle and more) to win the vacant IBF title, as well as two defenses against undefeated fighters. Finally, Ruiz ended up being a two time WBA titlist, who won fights over contenders Hasim Rahman and Andrew Golota.
Significant heavyweight fights when he was past his prime
Hasim Rahman - Beat Rahman by technical decision, who ended up winning an interim WBC title that was elevated to full status when Vitali Klitschko retired.
Nikolay Valuev - The same fighter who had been clearly outboxed by Chris Byrd six years before, knocked out by a shot, blown up former middleweight champ James Toney and widely outpointed by an underachieving Larry Donald, as well as Sultan Ibragimov received a WBO world title shot against the giant Valuev without having any recent good wins to justify it. However, in an amazing turn of events, Holyfield totally outboxes the Russian Giant only to lose a heinous majority decision that should have clearly gone to Holyfield.
Since the Valuev fight, Holyfield has beaten and equally shot Francois Botha and survived a fight that would have resulted in a sure loss to Sherman Williams because of an accidental headbutt before the fourth round, resulting in a no contest.
None of that is important, as Evander Holyfield has been putting off retirement, fighting on borrowed time since at least 2002. His career accomplishments at cruiserweight and heavyweight up until his last title win against John Ruiz have cemented his place in the Hall of Fame and given him the obvious distinction of all time great, not just at heavyweight, but pound for pound. It is often forgotten that Holyfield was so outsized by nearly everyone he fought after leaving cruiserweight, because he never really had a problem dealing with it. If that factor is added into the analysis of his career resume, it's value only goes up.
Add the sloppy win over Rahman and a bad decision against Valuev, and you have a career that can only be matched by those fighters or previous eras who had hundreds of fights, and a very elite club of those modern era fighters who followed the Holyfield method of choosing opposition (such as Ali and Sugar Ray Leonard), in always fighting the best possible opponent. He did not miss fighting a single elite fighter in either division throughout his prime, and the amount of contenders that he never squared off against during the first seventeen years of his career can be counted on one hand.
Absolutely incredible fighter.