Cherry, Notts County's last line of defence at home to Manchester City in the third round on Sunday, admits to an enduring weakness for the sultan of slapstick. While Nottingham Forest fans might argue that you need a sense of humour to play for County -bottom of the First Division after five successive defeats - Wisdom's art is about nothing if not the little man triumphing against all odds.
As such they provide an appropriate metaphor for the FA Cup, an institution responsible for most of the extremes in fortune in Cherry's CV. One tie, before his 600-match career was into double figures, saw him make the sort of gaffe that could have been choreographed by Wisdom.
Yet there was also the time, in 1991, when his technique, agility and sheer courage helped County to a famous 1-0 win and a quarter-final place. The team left shaking their heads that day? Manchester City.
The headlines celebrated "Cherry blossom time". However, his heroics would have surprised nobody who followed his early progress. Born into a Nottinghamshire mining family 35 years ago, he was snapped up by Derby and was soon sharing duties with John Lukic in the England youth side.
"I was fortunate because the two tournaments I went to with England were in Monaco and Las Palmas," Cherry recalled.
"My wife had some of my mementoes framed for me at Christmas, and in the middle there's a picture of the squad outside Prince Rainier's palace. Brian Clough, who I'd love to have played for at club level, was the joint manager. It seems ages ago now."
In 1981, Derby loaned their fledgling keeper out to Port Vale, then bottom of the Fourth Division, and they gave him his FA Cup debut at home to Enfield. In the replay, the part-timers were a goal up when Cherry charged out of his area to hoof clear a through-pass. At least that was the idea.
"The ball bobbled over my foot, I ended up on my backside as one of their forwards walked it in, and they went on to win 3-0," he said. "Looking back, you have to laugh, but it was embarrassing at the time, especially as it was shown on Sportsnight that night."
Many a young player has been broken by such a blunder. Cherry had made Derby's first-team jersey his own when, three years later, they brought Plymouth back to the Baseball Ground to contest a place in the semi-finals. The only goal of the tie came direct from a corner that crept in at Cherry's unguarded far post.
"The sad thing was that I'd stopped everything they threw at me down in Devon, and got singled out for praise on Match of the Day. Peter Taylor dropped me after that game, which was a bad decision."
He eventually moved on to Walsall, and Plymouth, of all clubs, before £70,000 brought him "home" to Meadow Lane. They have been a mercurial six years; Cherry played in the top flight after County won promotion in both his first two full seasons, only to
suffer instant relegation and the loss of key personnel.
When County met City four years ago, for instance, they were managed by Neil Warnock and fielded the likes of Tommy Johnson, Mark Draper and Craig Short. For all their talents, and not forgetting Gary Lund's goal, it was Cherry's defiance which made the difference.
He was certainly due a clean sheet against City, having encountered them in five cup matches - Littlewoods, Simod and FA - in which he leaked 19 goals. " Funnily enough, I didn't play at all badly in those games," Cherry said. "Twice with Plymouth I let in six at Maine Road, one time being just after City had thrashed Huddersfield 10-1. They were really buzzing and I think I kept it down to single figures.
"When we beat City here it showed how crazy football is, because I've had better games and conceded goals. I had all the luck I didn't have in the other games. Television concentrated on a double save, when Niall Quinn followed up a free-kick by Alan Harper, but the best was when Quinn was through one-on-one."
Two wins from Wembley, County went ahead at Tottenham." Then they equalised with a deflection," Cherry sighed, "and Gazza, who should've been sent off, got the winner." Spurs lifted the Cup, but County took revenge last autumn by beating them 3-0 in the Coca-Cola Cup.
That result sealed Ossie Ardiles's fate; it was also too little, too late for Warnock's successor, Mick Walker. Now it looks as if nothing less than an upset against City will extend Russell Slade's brief reign. Cherry may not be around to see how the situation develops. After the club withheld the contract he felt he deserved, he went on the transfer list.
"There's no reason why I shouldn't have several more years at a good level," he said.
"Look at Ogrizovic and Grobbelaar, both older than me. Or John Burridge, who's 43. I still work very hard at my trade."
Whatever the future holds for Cherry, City will find him determined to frustrate them again. Premiership quality ought to prevail, but that is what people thought last time. And since when did the Cup have any truck with conventional wisdom?