‘Why is the world so judgmental?’ Ian Holloway on painting, metal detecting and his 1,000th game

Ian Holloway is trawling through pictures of his artwork on his phone. “That’s Pep [Guardiola],” he says. “Threw that one away, punched a hole through it because I didn’t like it.” Vibrant, acrylic paintings of Brian Clough and Jürgen Klopp soon appear on the screen. Another, inspired by Leonardo da Vinci’s Lady with an Ermine, is of his wife, Kim, and their chihuahua, Ernie. “I couldn’t get her face how I wanted it, so she’s taken that over. I lost that one.”

There are drawings of Sir Alex Ferguson and Johan Cruyff, the latter puffing on a cigarette, a canvas of Walter White, best known as Heisenberg, and one of the Joker, which is on the wall of his son Will’s tattoo parlour in Bristol. “That’s what I was going to do. I wasn’t going to come back to football, I was going to do paintings for people. I had 100 people asking me online: ‘Can you do me a painting? How much will it cost?’ We went to see the Francis Bacon exhibition in London. Oh, what a weirdo but my God it was incredible. Art is just a wonderful thing.”

On Saturday Holloway will be in the same company as Clough, Ferguson and Klopp, by joining the select band of managers to have taken charge of at least 1,000 games, a club featuring 26 Englishmen, including Harry Redknapp, Roy Hodgson and Neil Warnock. For Holloway, who has managed in all the top four tiers, his greatest feat guiding Blackpool to the Premier League, the milestone match arrives in Swindon’s League Two game, as if by fate, at home to Grimsby, his previous club, from whom he resigned four years ago. The 61-year-old returned to the dugout last month at Swindon, fighting relegation to non-league. “I’ve got a helluva job on,” he says, estimating he has spent about 14,000 days immersed in football. “I’ve lived every emotion you could want – and it’s still not enough. It is the closest thing to a drug.”

Painting takes Holloway back to school in Oldland Common, south Gloucestershire, still life drawing with Mr Low. “I did this thing and I hated it. It was a toaster. He said: ‘It’s a reflective toaster, it’s metal, what can you see in it? Look, there’s one of your classmates there. The toaster is a lens to the world. What can you see in there, Ian?’ He went off, came back in and he said: ‘Oh my God, that’s the best thing you’ve ever done. Oh wow. Stop, have a look at what Ian’s done.’ And that never happened to me. Next thing you know he’s got it up in the corridor. Now you’re thinking: ‘The world’s your oyster, son.’ He loved his subject.” The same goes for Holloway and football. “It’s unhealthy not having it. You don’t feel right when you haven’t got it. I did a documentary, asking other managers because I thought I was the only one, I thought I was Tigger. I was missing it, I wanted it back, the importance of it. It’s weird.

“No one else cares about how someone else has got on, do they, really? But for you the world has stopped because you’ve lost. We love it and hate it. Where else can you get the [Sergio] Agüero moment? You wouldn’t watch the film because it would be unbelievable. For me, trying to fix something is the biggest challenge and the most fulfilling thing you can ever try and do.”

It all began at Bristol Rovers, whom he joined aged nine and who gave him his first taste of management. At 33, while “fit as hell”, he rejected a new deal at QPR to accept the role of player-manager at Rovers, his first game a win against Peterborough United in August 1996. “Talk about deep end … it was pretty scary, the feelings and emotions I had for the club probably didn’t help. I cared so much, probably too much. I took everything personally. If you spoke to the press dealing with me then it was: ‘What? Who? When?’ I was so aggressive. I got booked 17 times in the season, I’d be arguing with referees. The emotions of it all, I got totally carried away with it because I had my kit on … it was all too much. Looking back now, it was madness.”

What would the Holloway of back then think about hitting 1,000 games? “He wouldn’t have believed you – he struggled with believing in himself anyway. My life has always been a rollercoaster, just like the Big Dipper at Blackpool. I don’t want a smooth life. How boring would that be? And I meant it in a nice way when I said that myself and Blackpool look better in the dark. That’s why I like Brighton so much. Anyone can be whoever they want to be in Brighton. Why is the world so judgmental?”

The palette of conversation is, of course, wonderfully jumbled. Holloway tells how he and his wife are members of the Caravan and Motorhome Club, maximalists – “our house is like a museum, we’re total hoarders” – how they have upped sticks 48 times – “you should see our packing technique” – and the joy of metal detecting. “I’m the digger … you have to have the patience of a saint because it’s hours and hours of nothing happening.” Holloway zooms from 0-100mph in a way only he can. “You think: ‘God, it’s round, it’s giving a brilliant signal, it’s gold, it’s gold! … Damn, it’s a goddamn ring-pull.’ I’ve got millions of ‘em.”

Even taking account of his colourful character, it is surreal to hear Holloway talking about getting permission from local farmers to scour land in search of artefacts. “The problem is the first time I did it I walked about 10 yards and found this beautiful, massive coin. I thought it was going to be like that every time. We watch the Detectorists, we do all of that. Kim finds shards of pottery; to me it’s a broken pot, a handle off a cup … ‘This is slipware.’ I’m getting educated. I’m trying to give back the joy she has given me by being there. I’ve got a deckchair in the sun, I’ve got my hat on, and if she needs me I’m over and I’m digging. My wife might find a nail and it might be a Roman one and I’ve never seen anybody so chuffed in my life. It’s a bit rusty to me. ‘No, it’s lovely.’”

For a second, there are flashbacks to one of Holloway’s most famous soundbites. “I couldn’t be more chuffed if I were a badger at the start of the mating season,” he said after his QPR side beat Cardiff in 2005. More recently he went viral for insisting Swindon’s training ground is haunted but he has not asked Kim, a Pagan, to cleanse the site. “It is totally true, there are ghosts there. We’ve watched hours and hours of Most Haunted,” says Holloway, who has a spooky ringtone to match. “We paid to go into a dungeon in a haunted castle, in Warwick, and bugger-all happened.”

To some, Holloway is a national treasure. “If that’s the case, I don’t know where they dug me up. As you can tell, I get high on other people, I get high on life. How many times do you see it, you’re driving along, someone beeps, gives you that,” he says, flashing his middle finger. “Why? Why do we do that? Sorry mate, I don’t care what mood you’re in, you’re not affecting me. I don’t do that any more.” He has a few gripes, too. “Things are getting uncomfortably expensive and life is really bad for lots of people,” he says, citing the price of petrol, water and logs. “But I always believe in people. As my mum told me: ‘Always look for the good in people, son.’ I went: ‘Yeah, but.’ And she said: ‘Woah, woah, woah!’”

Holloway is desperate to get a win on Saturday to drag Swindon, two points above the drop zone, away from danger. “Oh my goodness, it is all that matters now,” he says. But beneath the surface there is a giddiness about the things he has experienced, the people he has met and the places it has taken him. “I feel totally privileged to think: ‘I’ve actually sat next to that fella.’ Daley Thompson a few months ago, oh my God, wow.

“Sharron Davies. Gianfranco Zola. Sam Warburton … life is unreal. Unbelievable. Jack Draper. I know him, I’ve met him, gave him a hug, he’s massive. I sent him a little text. ‘You can do it, son.’ I wish I could have a dinner party with all these people. Kenny Dalglish, what a bloke, what a player, what a person. Alan Ball, played with him at Bristol Rovers, what a bloke. Kevin Keegan, if I bumped into him I’d actually know him. He’d go: ‘All right, Ol?’ Wow! Wow! How I did that … it’s unreal. Little bloke from Longwell Green. Come on, it’s incredible.”

Holloway’s arms are decorated in ink. “He [Will] did his mum on my arm,” he says, rolling up the right sleeve of his camouflage jacket. “He was nervous. I’ve got [Muhammad] Ali, a Red Indian up there,” he says, pointing to his left shoulder, “an eagle, a gladiator riding a horse there. I wouldn’t have wanted to be a gladiator. You make a mistake in that arena and you’re dead. I said to the players last week [after defeat by Bradford City]: ‘Why are you so unhappy? We’ve had a great week. I know we should have drawn, but we didn’t.’ You have to take the small things. The event in your life plus your response equals the outcome, it’s quite simple.”

After chatting for 90 minutes, plus a stoppage for photos, the key bits have surely been boxed off? Holloway’s mind is whirring though, thinking about the progress his builders are making at his cottage. Swindon’s kit men are doing his washing while work continues at his Wiltshire base between Bath and Chippenham, near Box Tunnel. “Which Isambard Kingdom Brunel built,” he says. “It’s wonderful. But if a nuclear war happens, we’re dead, because there are tunnels there with our nuclear bombs in. We’d be gone in the initial blast. It’ll just be: ‘Boom!’”