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Alan Cumming at the premiere of The Hateful Eight in New York on Dec. 14, 2015.

KRISTA SCHLUETER/NYT

The last time Alan Cumming was in The Globe and Mail, he was winding up his final biweekly column in the Life & Arts section by sharing his thoughts on mortality: on quality of life, on something called "scrotal aging" and on the heartbreak of losing a beloved pet. Next weekend, he'll be at Toronto's Winter Garden Theatre to share some more: songs, showbiz gossip and a little bit of his soul, in Alan Cumming Sings Sappy Songs, a cabaret show he originally performed last year at New York's Café Carlyle. We spoke with him by phone.

Hold on, your two shows in Toronto are basically sold-out. Why are you bothering to talk to me?

I know, right? Because I'm a man of honour, and I agreed to do these interviews before the show was sold-out. I was prepared to whore myself out to sell tickets, and if I'm a whore then I should talk to you, even if there are no tickets left. "A noble whore!"

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Well, at least you're being honest.

I think in a way the overreaching theme of the show is about being authentic, being truthful. In order to do the show properly, I have to really connect to singing the songs and telling – you know, I tell quite intimate things. Some of the stories I tell are about the importance of being honest, and about being authentic.

You're certainly authentic in the photo on the cover of your new CD. Okay, scratch that: You're naked. With a couple of naked models. On the street in front of the Carlyle late at night, with only a champagne bottle obscuring your … um … How long were you actually out there?

Actually naked? Probably less than a minute. We'd practised it with our clothes on and, you know, dodged the security guard. But it's one of these things, kind of like when you're about to jump in to go skinny-dipping and – "Who's gonna be the first one to do it?" We were all ready, we knew it was about to happen, but the photographer was futzing, so I just took my clothes off and said, "Right, we're doing it right now," so everyone else had to. When you pull your pants down, other people go – "Oh!" And they take their clothes off, too.

Really? I can honestly say that's never happened to me.

Well, you should give it a try because it's kind of hilarious.

I think HR would have me out of the building pretty quickly.

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The Globe and Mail would be ruined!

That reminds me: On the website for your show, it says you've been called a "bawdy countercultural sprite."

Yeah, what does that mean?

I don't know any more.

"Countercultural" – "against culture." I mean, The New York Times guy said that. … But I couldn't be more mainstream in some ways: I'm in a TV show about lawyers, and I do things on Broadway. It's not that I'm doing agit-prop. I mean, I'm a big TVst– whatever – a famous person who takes their clothes off in front of a hotel at 2 o'clock in the morning. I get it, in terms of that.

Maybe in these cynical days just singing sappy songs is countercultural. Do you think we undervalue sappiness?

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I think sentiment is seen as a negative thing, when it's actually not. It's just a thing. "Overly sentimental" can be a negative.

Manipulative?

Manipulative. Or just – "sugary" more than manipulative. "Manipulative," sometimes I quite like. But sentiment, on its own, is a very important thing. Just let yourself feel something.

Not to go down a rabbit hole, and I know I've only got another few minutes –

The clock is ticking!

But, in the shows I've seen you in – Cabaret, Threepenny Opera – they are emotional, but there's also a Brechtian wariness of that emotion.

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In America, people are very scared to let go and to feel things. … I mean, that's why I did these songs. A lot of the songs that I did in Club Cumming, my club in my dressing room [after each performance of the recent Cabaret revival] … people would be like, "What is that? What's that song?" And I would say, "I'm not telling you until it's over. Just feel it and enjoy it … make a judgment based on what it is rather than how you think about it." That's such a dangerous–

Because we want to judge?

We want to know what we're supposed to think about something, rather than feel it. I just find that to be really numbing.

Your first show is midafternoon. Is there any difference between doing a 3 p.m. show and an 8 p.m. show?

People aren't drinking, basically, is the difference. Me included.

This interview has been condensed and edited.

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