After starting out with Motherwell, McCulloch won a move to Wigan Athletic in 2001 and played in the star-studded English top flight.
Capped for Scotland during his time down south, he then fulfilled a lifelong dream in 2007 when he returned home to sign for his boyhood heroes.
The versatile player has won every domestic honour with the Ibrox club in the last five years and enjoyed some memorable European nights.
But the flipside of that has also had him endure the considerable trauma of the Glasgow institution's off-field problems in the past nine months.
Big Jig was instrumental in the Rangers players agreeing to take a pay cut after their employers were put in administration in February to safeguard the jobs of non-playing staff.
And while many of his team- mates opted to move on to clubs in England and abroad, he had no hesitation in pledging his future to his beloved Govan club.
The 34-year-old, then, has packed more into his professional career than most other players.
None of it, though, has prepared the Gers skipper for the unvarnished raw life in the Irn-Bru Third Division this season.
"They must have different rules at this level," he said as he reflected on his eye-opening experiences in the fourth tier of Scottish football in recent weeks.
McCulloch was alluding to the rough treatment Ally McCoist's side has been subjected to, away from home especially, by their part-time opponents.
Goalkeeper Neil Alexander last week hit out at the lack of protection referees are giving his side from alleged foul play.
But the no-nonsense treatment meted out to Rangers has clearly not deterred the striker – he took his goals tally for the 2012/13 campaign to 13 with a second-half double in the 2-0 win over Queen's Park last Saturday.
Yet he admits that, with kids like Fraser Aird, Robbie Crawford, Barrie McKay and Lewis Macleod all being brought into the team, it has been a factor in their difficulties.
With another difficult game on the road against Clyde at Broadwood looming on Sunday, he knows Rangers will have to match their opponents' uncompromising attitude. However, McCulloch feels that is good for the development of the young players who have forced their way into the first team and is convinced they can now cope with that aspect of the league.
"It is a very, very physical league, he said. "Having been used to playing in the SPL, it has definitely been a bit of a shock to the system for a few of the boys.
"It has been hard with the number of young boys we have in our team. But this is a man's game and it is not a bad thing for the younger boys to experience.
"They have to learn how to play that style of football at times.
"The older players like myself have to help them of course. We are fine with it. We have needed to adjust to it.
"But we are on top of the league just now so I think we must be doing that alright. Personally, I am loving it."
One individual who has had no problems adjusting to the unique demands of the Third Division this season has been Andy Little. The Northern Ireland forward had netted eight times in as many games for Rangers before suffering a foot injury on international duty at the start of last month.
McCulloch was delighted to see him make his comeback when he came on as a substitute against Queen's.
He is hoping the 23-year-old will force his way back into McCoist's starting line-up soon and help them extend their slender lead – they are currently only ahead of Elgin City on goal difference – at the top of the league table.
He said: "Andy has got pace, he is direct and obviously he has been in among the goals during his time in the team this season. It is good to see him back, injury-free and looking sharp. He is a bit like myself in that he can play in midfield and up front.
"It is invaluable to the team to have players like that who can operate in different positions and do well in them too.
"Hopefully he can get back into the team and back on the scoresheet. Despite the number of goals I have been scoring, I am not exactly a prolific marksman. We need other guys to pitch in soon.
"Andy has shown what he is capable of in that department and hopefully he can pick up where he left off before he got his injury. He has shown he can score goals in whatever position the manager uses him in, whether it be out wide or up front."