Entered the Spotlight of Professional Wrestling: 1980 (in NJPW) Age 26
Should Have Exited the Spotlight of Professional Wrestling: 2005 (in WWE) Age 52
Let's start with the man many think is in most dire need of retirement. Hogan's surgeries mean that he can barely take any bumps at this point in his career, and many fans observe that the Hulkster was hardly a good wrestler in the first place, merely a charismatic showman, and that he needs to stop relying on that now what little skill he had has diminished.
At age 47, it was August of 2000, a month after Hogan's infamous argument with Vince Russo at that year's incarnation of WCW's Bash at the Beach.
Arguably, the situation was not Hogan's fault—Russo instructed Jeff Jarrett to lie down and hand his World Title to Hogan. Russo and Hogan had an on-air argument about it, resulting in Hogan's departure from WCW.
Rather conveniently for Hogan, this meant he left the company as the company's situation went from bad to disastrous, allowing him to sit out the company's lowest period, making his return to the WWE much more impressive.
2002-2003 saw Hogan return to WWE, where Hulkamania had first run wild. The original NWO—Hogan, Hall and Nash—reformed to play havoc on the two top Attitude Era faces of the WWE—The Rock and Stone Cold Steve Austin, leading to a tag-team match between the NWO and the WWE faces, and a WrestleMania main event between Hogan and The Rock.
That match alone justifies Hogan's continued wrestling past the age of 47—the promos were excellent, the Raw tag-team match-up was great, and the match itself was excellent, with the two men shaking hands in respect at the end. The clashing of eras, the passing of the torch, giving something back to the company he had quit—it was all rather symbolic and special.
Hogan entered the match as a heel, but crowd support was so great he left it as a face. Hogan then feuded with all of the top figures in the WWE one after the other—defeating Triple H to win the WWE's world title of the time, the Undisputed Championship, holding it for 28 days. Fittingly for the man who put the name WWF on the map, he was the last man to hold the world title before its change to WWE.
Subsequent feuds included The Undertaker, Kurt Angle, Brock Lesnar, a rematch with The Rock and another major WrestleMania match against Vince McMahon. Hogan also very briefly held the World Tag Team Championship—for the first time—with Edge.
Hogan vs. Lesnar saw Hogan take some serious damage, showing he was still in good condition, and when this was arguably where things started to go stale. WWE used the Mr. America gimmick as an attempt to keep the Hogan character—which had run its course, having turned face, gone toe-to-toe with the top men in the company reclaimed the Undisputed Championship and defeated Vince McMahon—and really, it was all a bit naff.
Seeing Hogan revisit his decades old feud with Roddy Piper was quite fun, but little else.
Hogan left to join TNA, but after setting up a feud with a promo, injuries meant he was uanble to, and he ultimately returned to WWE from 2005-2006. The most memorable parts of this period were Hogan's WWE Hall of Fame induction, brief tag team with Shawn Michaels and feuds with Shawn Michael.
Also of note was an episode of Raw which featured a truly star-filled tag-team match—Tyson Tomko, Chris Jericho and Christian vs. John Cena, Shawn Michaels and Hulk Hogan.
After a solid 2005, Hogan did little within WWE in 2006, and his WWE career wrapped up with a really awkward feud with Randy Orton, which attempted to sell Hogan's reality TV career and Orton's Legend Killer gimmick at the same time and simply did not work.
Following this, Hogan would embark on some poor one-off matches, his Hulkamania Tour of Australia (don't look it up, it's not pretty) before joining TNA. In TNA, he has proven he can still pull off promos, still garner a fan reaction at matches but also really can't wrestle and is very in touch with the sort of product desired by modern audiences.
There is still something of a place in wrestling for Hogan—if he would appear very rarely and take no behind the scenes role.