Jack Whitehall: I’ll always be posh. I still have a man-child streak

“I still have this streak that is a bit of a man-child stuck in arrested development,” he admits on a Zoom call last thing on a Thursday afternoon in April. “But I am also trying to live up to the high standards set by other family members, peers and friends and people in my life who have maybe arrived at their more mature period of their lives a little more hastily than I have.”

It’s the end of a day of press for Whitehall in support of his latest stand-up tour, Settle Down, which is currently travelling around the country and which comes to Glasgow next month. Yesterday he flew in from America just in time to watch his team Arsenal get thumped by Manchester City. “Sporting torture,” he says. (The Spurs fan in me doesn’t rub it in. Well, not too much.)

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He is on close-up on Zoom, “posh hair” and all. Whatever posh hair might be. It’s certainly Timotei lush and floppy of fringe. And the accompanying beard is well maintained.

He’s well lit too, certainly in comparison with the Soviet-style lighting I seem to get on Zoom.

“You need a ring light,” he tells me. Professional tip.

His new stand-up show, Settle Down, offers exactly what it says on the label. “A lot has happened in the four years since I toured last,” he points out. “I’ve met my life partner and we’ve moved in together and we’ve got the house, the mortgage and the dog. Very grown up things and I feel like I’m edging into a new phase in my life.

“And it’s all about my sometimes reluctant acceptance of that and my growing old disgracefully.”

Whitehall lives with his life partner Roxy Horner and Coco the cavapoo in west London in a house worth, depending on which tabloid you believe, either £12 million or £17.5m. A substantial mortgage in either case. He has also recently announced he and Horner are expecting their first baby.

All of which does sound very grown up. But what does that mean to him? Jack, I ask, what is your definition of adulthood?

Jack Whitehall in Bad Education (Image: free)

He looks around and thinks about the question before replying.

“Just because I can see it in front of me off camera, I’ll get anxious when I see glasses or mugs on tables that don’t have coasters underneath them. It genuinely gives me a little bit of anxiety when I see a mug connecting with a table bareback. I think that’s a sign that you’ve reached a stage in your life where you’re thinking about stuff like that.”

There are other signs too, he says. He’s into napping these days, much to his partner’s annoyance. “My girlfriend is an insomniac. We’re totally mismatched on that level and she finds it infuriating that I can sleep anywhere and at any time and that I’m constantly looking for opportunities. That is a constant bugbear of hers.”

Oh, and he reckons he’s a bit more adult in his attitude to alcohol too.

“I think I’m a more grown-up drinker now. I used to be a binge drinker. Now I have one glass of wine during the week to take the edge off. Which I think is quite grown up. I still binge-drink at the weekend. I basically have a run-up to it. You usually need to prepare at my age.”

Let’s just remind ourselves that Whitehall is a massively ancient 34. His bus pass is a way off yet. But perhaps his edging towards middle age is such a surprise – to us and maybe to him too – because youth, and a particular brand of loud, show-offy, even bratty and certainly entitled youth at that, was the currency he traded in for so long, whether on stage or on screen (though he’s always been at pains to point out that he is nowhere near as much of an arse as JP, his character in Channel 4’s comedy Fresh Meat).

“When I first started doing stand-up, because I started so young, all my shtick was all about how young I was. That was my gimmick and I remember being very aware that that was going to run out very quickly. It would be a well that would run dry before I knew it.

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“And it was around that time that I had been adopting a mockney accent when I was onstage as well because I was so embarrassed that I was posh and didn’t think that would be a good thing to reveal to an audience. And then I came to this realisation that the ‘being young’ thing wasn’t the angle to mine and I should just own being a toff and use that as my comic persona … And then spent about 10 years flogging that dead horse.”

Youth is a currency that inevitably gets spent. Poshness has more of a shelf life.

“I’ll always be posh,” he suggests. “This show is hopefully a little less reliant on that. I feel like, whilst I am still clearly posh and there are references to boarding school and Waitrose and what not, it’s not the punchline so much as it used to be.”

Ah yes, boarding school. His parents – theatrical agent Michael Whitehall and actor Hilary Gish – famously packed Whitehall off to one, aged 11. He then went to Marlborough College in Wiltshire, a private school where Kate Middleton was also a student.

This is part of his posh past he’s never been quite as keen to embrace. “You get a swelling sense of guilt, I guess,” he told Young on Desert Island Discs. “You can’t not consciously think it’s ridiculous that some schools have no sports fields and I went to a school that had a beagling lodge.”

Today, when his boarding school years come up, it’s because he has been wondering if they were in fact a brake on his becoming an adult.

Jack Whitehall (left) alongside his father Michael (Image: free)

“Boarding school certainly does not prepare you particularly well for adulthood because you are just mollycoddled. It’s a very unrealistic environment to raise a child. So, yeah, I definitely feel like there are poor habits that I’ve got from having gone to a boarding school that I definitely wouldn’t want to have instilled in any children I might have in the future.

“I know my girlfriend certainly doesn’t. There have been lots of discussions about that. Lots of arguments.”

Quite often, he suggests when some foible or other of his comes up, she’ll ask: “Is that a boarding school thing?”

Still, boarding school did help instil an enviable sense of self-confidence in him. Whitehall was, he agrees, something of a precocious young man. That might have been a useful shield for his early days in stand-up, he suggests.

“Probably the precociousness means that you also have an elevated sense of how well it’s going in those early stages, which is quite helpful because there were a lot of gigs when it wasn’t working and I didn’t know what I was doing. But I loved doing it so much. I fell hard for stand-up and was so determined that this would be my career and my course in life. I really held onto that even when I wasn’t killing at gigs. I felt I could get better at this.

“I was a bit naive and if I was starting now I would have a more cynical head on my shoulders and the reality of it might have hit me a little bit harder and hampered me. I always say when people ask me for advice about doing comedy – the most important thing is you have to have the hide of a rhinoceros. Because when you first start you won’t be the finished article. You will be a work in progress for a long time.”

What was it about comedy that attracted him in the first place? “I loved making people laugh. I had always been drawn to that. I’ve always been a bit of a clown, I guess. I was quite awkward in other ways and quite insecure as a person when I was in my early teens and I found that making people laugh was a mechanism to connect with people. I guess that’s how I discovered comedy and stand-up.”

The Edinburgh Festival Fringe may not have the same cachet as it did even 15 years ago in launching comedy careers, but it was vital for Whitehall who was still a teenager when he first made his way north.

“I am so pleased that I cut my teeth at Edinburgh and I was having to do a show to a paying audience every night and being mullered by critics and having discerning peers come and watch it, and seeing other comedians and learning from them. It was such an amazing environment to develop as a comedian.”

Did you get reviewed in those early days? “Oh, horrendous reviews. The first show I ever did I got one star from Chortle which is the holy grail of comedy reviews when you are starting out. They said I gave an impression of what I thought a stand-up was.”

How has his comedy changed over the years, I wonder? In the midst of the current culture wars has he become more cautious?

“A little bit. There’s definitely a little bit of policing. I don’t know whether that’s necessarily to do with where the culture’s at. It’s more that I feel I’ve matured a little bit as a comedian. There are certain things I don’t want to say. I try to be a little bit stricter with myself about punching down, because I feel like probably in the past I have done that. I just interrogate my material a bit more than I used to, which is not to say that occasionally I’m sure I’ll have the odd misfire in the developing process of jokes.

“But I’m not necessarily an edgelord comedian trying to shock people, so I think I am in slightly safer territory with that anyway and I also take solace in the fact that if I’m going to get cancelled for a joke I’ve probably told it. It’s already out there floating in the ether. Or in my case my dad’s probably already told it. That will be the one that comes back to bite me.”

Ah yes, his outspoken dad Michael has become a star on the back of Whitehall’s fame thanks to Travels With My Father on Netflix. He’s been thinking about his parents more now that he’s in this new grown-up part of his life.

“I do admire that they’ve managed to stay together and built a relatively happy relationship as well, albeit with a few bumps in the road along the way. I do think my mother has the patience of a saint. He’s so lucky to have met her. Relationships take a lot of work and sometimes I think it’s miraculous that they are happily married after all these years. But as I get older I am like, ‘Oh, it’s interesting to think about what it is about their relationship that does work and if there are lessons that I can glean from it.’ Certainly I’m more aware of that than I used to be.”

The last few years have seen Whitehall diversify. After working his way up through comedy panel shows to roles in comedy dramas such as Fresh Meat and Bad Education (which he wrote himself) he has now graduated to Hollywood. Is actor Jack a different person than stand-up Jack?

“Ah yeah, I guess so. On-set I tend to feel a bit more insecure and a bit more needy. I ask a lot of questions and worry maybe a bit more. With stand-up I feel more naturally at home when I’m doing it. I just feel a little bit more out of my comfort zone when I’m acting, especially if it’s something that is not broad comedy.”

His co-stars can help with that. “On Jungle Cruise, Emily Blunt and Dwayne Johnson were both great because they had no real ego at all and both had fantastic senses of humour and quite childish humour as well. We were three very kindred spirits talking crap basically for the duration of this three-month shoot. I felt very at ease in what was potentially a very intimidating environment because they just made it feel like we were three kids sat at the back of the class. I found that experience far less terrifying than it should have been.”

What I want to know, Jack, I tell him, is – will Julia Roberts (whom he starred alongside in the 2016 film Mother’s Day) be sending him a birthday card?

“I was very intimidated by her,” he replies. “I kept forgetting my lines and she kept having to give me line cues which was so embarrassing. I was just staring at her in scenes and forgetting my cues and she would be like, ‘Jack, it’s your line.’ She would know my line and had to give me prompts. I was a little too inexperienced when I did that movie to behave like a professional. That was definitely a learning moment. Know your lines.”

He has another movie coming soon, Robots, in which he co-stars with Shailene Woodley and a role in the second series of US murder mystery comedy drama The Afterparty, which is due to air on Apple TV+ in the summer. But for now the stand-up tour is the thing. He has missed it, he admits. “To be honest, what with the pandemic I had a year and a half off from doing anything on stage and so getting back up in front of an audience, I have appreciated it even more so this time.

“And I love that immediacy of doing stand-up. I’ve been doing TV and film, which can be arduous sometimes and a slow process and I really miss that ability to have an idea or a thought in the afternoon and then be onstage a couple of hours later and releasing it into the world.

Is there a downside? “The worst thing about being on tour is probably the tour lifestyle. I eat crap and drink after most shows because I find it hard to come down from the adrenalin of it all. There is a lot of travelling. Late nights, early starts. I just feel myself deteriorating over the course of a tour. And then it’s always annoying because you have to record a Netflix special right at the end of it when your soul has left your body and you are running on empty and have been eating Greggs for a month. It’s not an ideal time to be then put on camera.”

He looks at me, smiles that posh boy smile. “But they can do lots of things in the edit now.”

Jack Whitehall: Settle Down plays the SEC Hydro, Glasgow, on June 19. He is also at the Edinburgh Playhouse on August 20 and 21.