‘Go to Hollywood!’ – that time Jack Dee offered me career advice

Jack Dee is that comedian Off the Telly, which also happens to be the title of his latest stand-up tour, heading to Scotland next month.

Once described as the “nation’s most loved curmudgeon” (isn’t that a great word?), I have to admit I wasn’t sure how an interview with the poker-faced comedy favourite would go, but not only was he hilarious, he also offered me some, erm, valuable career advice. And no, it wasn’t to quit, as I fully expect someone to Tweet me. Cheek.

During lockdown, Jack took on the role of agony uncle, answering fans’ life dilemmas in a brilliant book entitled What’s Your Problem.

So brilliant is it that Jack is pretty sure it’s available now in all good charity shops’ bargain buckets.

“There’s a bit of tough love in the book. People have written in with their problems and I’ve given them a way out and it’s available in all good charity shops. The paperback is going for 20p – I like to think I’m supporting Macmillan (cancer charity). 20p and that’s a Kit Kat for a nurse.”

So, when in front of the agony guru himself, it seemed only right that I seize the opportunity to garner his expertise on a question of my own – or a question on behalf of a ‘friend’. Yes, the old ‘asking for a friend’ technique…

“Hypothetically speaking, how should an entertainment reporter, who reports on a show all about entertainment in Scotland, go about asking their bosses for a pay rise?”

Without batting an eyelid, Jack replied: “Someone as good as the person you’re describing, I think has a future in Hollywood anyway, so lay that on the line. ‘Give me more money or I’m off. I’m off to Hollywood. They want me there – do you want me here?’.”

If you never see me on your TV screens again, you know why!

It was just one of many very funny moments during the chat and I know fans are in for a treat when Jack comes to Dundee, Arbroath, Dunfermline and more, from October 6.

No stranger to performing in Scotland, he actually tested out his material for this show in small venues across the country back in 2018.

“I had a great time just going around on my own, finding these little places that would have maybe 200-300 people come and see me and it’s a great testing ground for material cause up in Scotland there’s an instinct for it. They’re not going to laugh at anything, but if it’s funny they’ll laugh, so they’re perfect for it.”

There will be plenty of laughs if you’ve got a ticket to see him Off the Telly – that I can guarantee.

What’s On Scotland is on STV and the STV Player at 7pm tonight on September 9.