Attempting to steer Leeds United towards a brighter future has not exactly, in recent years, been a laughing matter.
The Elland Road club's travails during the on-going fightback from what was supposed to be a cautionary tale for the rest of football have been such that even the most optimistic of individuals would have found it hard to maintain a smile for too long.
For Ken Bates and Simon Grayson, however, the pressure and stress that comes with the task of reviving the club's fortunes has not prevented the pair from enjoying their fair share of fun along the way.
Spend any time in the company of the men at the helm of United and it is clear they both regard each other fondly. One-liners and cutting remarks abound, such as the time they were discussing the release of the film, The Damned United, and Grayson made an innocent comment about having already lasted more than Brian Clough's 44 days – to which his chairman replied, 'You nearly didn't after we lost at Hereford'.
Likewise, a few months later Grayson could not resist the opportunity to get his own back when, after hearing that Bates had first met his wife – and one-time journalist – Susannah when she interviewed him, he quipped: "Yes, but she was a policewoman at the time."
The two men clearly share an irreverent sense of humour and a close bond, which in turn is helping transform United's fortunes. In the two years since Grayson took charge of the club where it all began for him as a teenage apprentice, United have soared from ninth in League One to the automatic promotion places in the Championship.
Throw in a first win at Old Trafford for almost 30 years and a thrilling draw against Tottenham Hotspur in the FA Cup and it is no wonder Bates is so pleased with the man he lured away from Blackpool to replace Gary McAllister.
"What I like about Simon is that he is not flashy," says the 79-year-old United chairman ahead of the Boxing Day visit to Leicester City. "He is someone who isn't always wanting to get himself on the television or in the newspapers, unlike a lot of people I could mention.
"He just likes getting on with his job. When he came in, it was quite a culture change for everyone. Unfortunately, it had not worked out under Gary and the team was struggling. Confidence was low among the players but Simon came in and quietly got on with the task.
"I enjoy working with Simon and am 100 per cent behind him. I don't expect us to always win and play at our best every week, that just isn't realistic in football. But what I like about the job Simon is doing is that he has got us playing a pleasing style of football with a degree of style.
"As well as the good football we play, the team is also packed full of fighters who give their all. That is what we want because that has always been what Leeds United has been about.
"It has taken time to mould the squad into his own image but I think he has now done that. It started with making sure he got the backroom staff he wanted. He made a clean sweep and started again.
"Two years on, we can see the fruits of the decisions he took then."
On his own relationship with the United manager, Bates said: "In the two years we have worked together, I can't remember us ever having a row. What we have had, though, is a lot of laughs,
"We both possess a similar sense of humour. He is a bit quicker than me and I am a bit more mature so we balance each other out.
"At the start of last week, for instance, I was speaking to Simon and he told me that after attending that day's hospital visit with the players, he would be taking all the staff out for a meal.
"I said to Simon, 'I will buy the champagne', to which he replied quick as a flash, 'Ten bottles? That's nice of you, Chairman.' I laughed and said to him, 'Oh, it's just my luck that I have got a manager who is deaf and can't count'."
Grayson was a rank outsider when the bookmakers drew up a list of potential candidates to replace McAllister after a five-game losing run that included defeat to Histon in the FA Cup had cost the Scot his job.
Two years on, however, there cannot be many managers more bulletproof in the entire country than the 41-year-old who last January was wanted by Burnley to replace Owen Coyle.
Bates said: "We all know Simon was approached and offered a job earlier this year. It would have been on a lot more money than he is on now but Simon said to me, 'I want to stay and finish the job'. That said a lot about him and how he feels about Leeds United."
On how the season is shaping up for Grayson's men, Bates added: "I am pleased. We were all a bit despondent earlier in the season when we were 14th but I always said this division would be tight until Christmas, when it would start to spread out. That is now happening."
It is not just in the Championship where excitement is growing in Leeds but also the FA Cup after Grayson's side were handed a first visit to Arsenal's Emirates Stadium in the third round.
Bates said: "For monetary reasons, it is good news for the club while in football terms it gives us the chance to pit ourselves against Arsenal.
"Last season, we played Manchester United, Tottenham Hotspur and Liverpool, and in those three games we showed we can hold our own with the big clubs. This will be another big test for us but, as no-one expects us to win, there will be no pressure. In many ways, it will be just like going to Manchester United in the third round last season."