Fry wasn't the first footballer to squander his youth on gambling and going to nightclubs, and nor was he the last. But unlike most who prefer that way of life to training hard and keeping fit, Fry has had the chance and the inclination to make up for it in management. And, at 50, he says the desire to do just that is what motivates him as he aims to take his biggest step so far by leading Birmingham City into the Premiership.
When the Endsleigh League season gets under way on Saturday, no First Division club, with the possible exception of Wolverhampton Wanderers, will have more ambition, or resources, or fans, than Birmingham. St Andrew's has been rebuilt at a cost of pounds 10m. Their gates in the Second Division last season averaged 18,000, higher than six Premiership clubs. They have sold pounds 2.5m-worth of season tickets for 1995-96. They have to be taken seriously.
But can the same be said of Fry? Can this heir to football's cheeky-chappie tradition, whose earthy wit and inexhaustible capacity for self-dramatisation have for so long illuminated the lower division scene, really be a Premiership manager in the making?
The only name Fry comes up with when you ask him which managers he most admires is Ron Atkinson. Fry and Atkinson, both ready with a quip and with a tremendous feeling for flair, have their likenesses, but there are times when, beneath the bluster and the bonhomie, Fry betrays a sense of insecurity.
For example, towards the end of last season, when Birmingham had a match at home to their promotion rivals Brentford, and Trevor Francis, then the manager of Sheffield Wednesday, turned up as a guest in the boardroom. Fry spotted him, and put two and two together. It didn't help that at the time he wasn't feeling appreciated by his board of directors. The atmosphere at the club, which was so close to getting back to the First Division a year after they had been relegated, was one of anxiety as much as hope. The Brentford game was a big one. Not many guest passes were issued because there were so many fans who wanted to be there. And then Francis turned up.
"I felt they were trying to get rid of me," Fry said. "I wasn't seeing much of the board. I didn't know what they were thinking. I started imagining things." After the season ended, Fry dallied with the idea of going off to manage Derby County. But then Karren Brady, Birmingham's managing director, stepped in. "We had a bit of a board meeting," Fry said. "I'd got it all wrong. I was getting worked up for no reason. I was forgetting Trevor is a legend at this place."
Now, Fry said, he must be the envy of most managers because of the way the board - principally the publisher David Sullivan, who owns the club, and the 26-year-old Brady - have backed him. "They wanted me to sell my captain Liam Daish," Fry said. "We might have got pounds 2m for him. He only cost pounds 50,000. They could see it was good business. But I said no way, he's my captain, he's crucial to my team. And they backed me."
Fry, Sullivan and Brady - "I've got a lot of respect for her, she's ruthless" - form one of the more unlikely triumvirates in football, in which Fry plays to the full the part of the little man battling against the odds, outspoken one minute, victim the next. "We knock things about a bit," Fry said. "And that's healthy, I think. The press like to play us off against one another." Fry is thus a vital ingredient in the Birmingham City soap opera that has kept the club's profile high at a time when, with Aston Villa going through a sticky patch and West Bromwich Albion stagnating, first place in the Second City is up for grabs.
If that sounds incongruous - Fry is still very much associated with football's small-time and the 14 volatile years he spent taking Barnet into the League - it is worth remembering, though not many do, that he has had a glimpse of glory before. As a teenager in the early Sixties, he had four seasons in the Manchester United reserves, a nippy inside forward who caught Busby's eye. But, Fry said, he never made the grade because he never gave himself the chance to.
In Manchester, the counter attractions of horses at Haydock and dogs at Salford proved hard to resist. "Now if I see my players going that way, I tell them it's all right in moderation. You've got your whole life ahead of you. I don't want to stop you enjoying yourself, but you don't want to end up like me - 50, sitting in your armchair chewing your brains out because you ruined a good career."
Fry also played for Bolton, Luton and Leyton Orient before he started out in management at non-League level. His time in charge at Barnet, in two spells, were characterised by seemingly never-ending battles with the club chairman, Stan Flashman. There followed a brief spell at Second Division Southend before Birmingham, struggling near the bottom of the First Division, came in with their offer at the end of 1993, Fry felt it was too good an opportunity to turn down.
"You're limited in what you can do at clubs like Barnet and Southend," Fry said. "You're not limited at Birmingham. There were problems, mind. They'd had seven managers in the previous 10 years or so. When I joined them they were sixth from bottom. They'd lost their last six games on the trot. By the time I got it right it was too late. In our last 10 games, we won six, drew three and lost one. Went down on goals scored. To be fair I'd let the club down."
In retrospect, some people at St Andrew's, though Fry isn't one of them, might almost have felt it was worth going down given the free-scoring triumphs of last season when Birmingham won the Second Division as well as the Auto Windscreens Shield, to the final of which at Wembley they brought 51,000 fans. So wholeheartedly did Birmingham throw themselves into the competition, attracting big crowds to their home ties by lowering ticket prices, that its sponsors now sponsor them. They recognised a team that shared Fry's ability to communicate with the public.
"I'm a fan at heart," Fry said. "I feel for them. That's why I've always wanted to entertain, always wanted my teams to score goals. I want everyone to go home happy." But can you entertain your way into the Premiership? "I don't see why not. We'll give it a go. I think it will help that teams will want to come and beat us."
Apart from his own team, who else does Fry fancy? "Norwich and Wolves," he said. "They're a class apart. Norwich are a good passing side, they've got pace, and I think Martin O'Neill has made the right move at the right time. And Wolves because Graham Taylor has done everything at club level and might have gone up last year if it hadn't been for injuries." Fry will have an early opportunity to gauge his own side's worth - Birmingham's first three home matches are all against clubs relegated from the Premiership last season, Ipswich, Norwich and Crystal Palace.
Fry, noted for unearthing talent from the lower reaches, was tempted to splash out on a big name during the summer, and came close to signing the Swedish international Kennet Andersson. But that would have used up nearly all the pounds 2m at his disposal and with three key players - David Barnett, Peter Shearer and Kevin Francis - suffering long-term injuries, he felt he needed wider cover and ended up making eight signings, all from the lower divisions. These include Ian Muir from Tranmere and Ken Charlery from Peterborough, both proven goalscorers.
As Fry rattles off the details about these players - his power of statistical recall is remarkable - it is clear just how wrapped up he is in the game. But that takes its toll on someone in whom there is clearly a melancholy streak. Fry had to force himself to take a week's holiday during the summer. "I was so stressed out," he said. "But my holiday really is standing in the sunshine watching the lads train pre-season." Now for the real work.