From Manchester United legend George Best to current Premier League star Declan Rice and everyone's favourite commentator, Chris Kamara, Stelling has shaken hands with them all.
Now, the iconic football host is taking on his next new exciting chapter as talkSPORT Breakfast host.
Every Monday and Tuesday he will join forces with another lovable football personality in Ally McCoist.
So who are football's nice guys, what was Best like and is Phil Thompson as scary as he seemed on the touchline?
No is the answer when asked about who the nicest people he's met in football are.
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He tells talkSPORT.com why below.
THOMMO MAY SURPRISE YOU
"Phil Thompson is one of the nicest men I've ever met despite the fact that when he was on the touchline as assistant manager to Gerard Houllier, or when he took over at Liverpool when Gerard was ill, he would bark out all sorts of message, you know.
"He'd wind the opposition managers up and the opposition fans as well! But he's the nicest man in the world you know, so he'd definitely be one of those."
MISUNDERSTOOD BESTIE
The late George Best was one of the nicest guys you could meet as scores of United fans will probably tell you, too.
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Best was plagued by alcoholism and died at the age of 59 in 2005.
"Wonderful footballer/ slightly misunderstood man. So many attributes - reliability wasn't one of them.
"So, sometimes he wouldn't show up for the show. [He was] Quiet, mild mannered.
"Not the showman that everyone saw when he was out on the football pitch. You know, they called him the fifth Beatle but he wasn't like that in those days. He was a very, very nice man indeed."
But what about legends he hasn't worked with and who don't play for his beloved Hartlepool United?
One Arsenal and England midfielder springs to mind.
RICE GUY DEC
"Declan Rice is a very nice, unassuming man for a super star footballer.
"When you've got that much, that young, it must be very easy to get carried away.
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"We see it with some people, but when I met Declan only a couple of times, I found him to be nicely understated and just a pleasant guy."