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Management
Executive of the Week: Meet Darren Gilmore, the Canadian Manager Behind the Scenes of Hilary Duff's Chart-Topping Comeback
Working with artists like Mother Mother and Boy Golden, the president of Watchdog Management has used his veteran experience in the Canadian music industry to help orchestrate the comeback of the year so far and the No. 1 success of Duff's new album Luck... Or Something.
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Hilary Duff is back, and her comeback is one of the best-executed in years — especially in Canada.
Her new album, Luck… Or Something, debuted last week at No. 1 on the Billboard Canadian Albums chart, a feat she hadn't achieved in more than two decades. Building on the buzz of her intimate show at History in Toronto earlier this year that had the whole country buzzing, she's now coming to 10 different Canadian cities on her Lucky Me World Tour in 2026 and 2027.
While the press run has played into the humour and nostalgia of the singer and actor's 2000s-era pop star tabloid days and viral low-energy "With Love" dance moves, her comeback has been more than a novelty. It's been orchestrated. With strategic rollout plans, a "dream team" of people working behind the scenes and a critically acclaimed set of songs that builds a space for grown-up pop on the global stage, Duff's new act is resonating in a big way.
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But there's a reason it's hitting so well in Canada: Duff's management is Canadian. Led by industry veteran Darren Gilmore, she has a sure hand helping guide her. The president of Watchdog Management, the Vancouver native has worked closely with management legends like Bruce Allen and Sam Feldman, and now handles a roster that includes a strong set of Canadian acts including Mother Mother (who have also built a second act into major worldwide success), Peach Pit, country singer Corb Lund and new Billboard Canada Airplay charts leader Boy Golden, among others.
When we reach Gilmore for this Executive of the Week interview, he's just gotten off the set of The Tonight Show, where Hilary Duff performed her new hit "Roommates" and taught Jimmy Fallon the "With Love" dance. Amidst the busy promotional tour, he finds some time to talk about the whirlwind rollout and why, beyond any 21st century viral marketing, the secret sauce is simple: make good music.
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Hilary Duff debuted at No. 1 on the Billboard Canadian Albums chart last week. How have you felt about the success of this comeback?
There’s so much happening for Hilary right now. Having been out of the music space for a number of years, coming back with a new record and the global tour, all at an A-level, all at the same time — that’s pretty unheard of in the business.
And honestly, she deserves it. She's an incredible human being, mother, artist, songwriter and personality. She made a hell of a record with her husband [singer, songwriter and producer Matthew Koma], who's an amazing talent in his own right.
You’ve been in the management business for decades, but this seems like a unique partnership. How did you first start working with Hilary Duff?
I managed her husband for damn near 20 years. They're like my kids. I was around when they first met, when he started working with her as a writer-producer 12 years ago, through the entire process of them meeting and dating, getting married, starting a family.
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It started out with me wanting to help them out as they were very quietly making this record and planning new music. There was no record company, it was just us very quietly making this plan. There was a lot of trust on her end, and she wanted to make sure that she surrounded herself with the right people. We have a tremendous team. It’s a career honour for me and we're having a blast together.
Other singers of the same era have attempted a comeback with less success. What do you think has set her apart?
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She's an icon and a superstar, but I think a big differentiator with this one is that the album is truly special. There are lots of artists who have a nostalgia moment and come back. There's some demand because there's been scarcity and they've been out of the market for a while. But this one is quite unique. She has such a clear vision musically for what she wants it to feel like: the lyrics, the words, the concepts, where she's at in her life as a woman, as a mother, as an artist.
It is challenging to come back in pop music, and especially to make cool, age-appropriate pop music that feels special and stands out and resonates. She's done it.
How much planning went into the rollout to make sure it would hit the way it did?
It's all been strategized right from the very beginning – every partner that we were working with, every opportunity in the setup around our shows, the record, the press we chose, the singles, the creative that we worked with, It was all strategized. It has all been a master plan. And then, of course, everyone catches some lightning bolts along the way.
How hands-on are you in all of those decisions and how hands-on is Hilary?
All hands 100%. I am involved in absolutely everything. So is she. She's an incredibly intelligent, consummate businesswoman. She knows her s–t, and at the same time, she's very trusting of her team. We surrounded her with the best in the world.
We have amazing partners in Atlantic Records, in Live Nation. Those are some of our dear friends from the old country, as I say — a lot of them are Canadian. It's funny sometimes, having come up with a lot of these guys and now they're some of the most powerful people in the music business. They're still old friends from the old country. Colin Lewis, who's from Toronto, has done such an exceptional job on the global touring end, and Erik Hoffman who [is the president of music at] Live Nation Canada has been deeply involved as well, even internationally.
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On the agency end, CAA has been incredible to deal with and they've done an excellent job from top to bottom, involved in all aspects of her career. My dear friend Kenny Meiselas, her attorney who helped me get started in the business a billion years ago, he's been great. Phil Sarna, her business manager who I've worked with for 20 plus years as well. We’ve got a real dream team.
The album debuted at No. 1 in Canada. With you behind the scenes and so many Canadians involved, would you say that played a role in the album’s popularity in this country?
Hilary has had a great Canadian audience for a long time, same with Australia, same with South America and the U.K. Along with Atlantic, I am fortunate to have some really strong relationships at Warner Music Canada [who released the album in Canada], and now I have other artists there, like Mother Mother, Jade LeMac, Donovan Woods. Eric Wong, who now runs Warner Canada from New York, has been an incredibly close friend for a long time and a huge supporter for decades now. Madelaine Napoleone, who is the head of marketing [now co-GM], she's a close friend. They did an excellent job and they've been really involved. We love to see it.
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Hilary Duff’s show at History in Toronto felt like the hot ticket of the year so far and helped to build the buzz. Can you tell me about that Small Rooms, Big Nerves tour?
We did four underplays: Shepherd's Bush Empire in London, then came to Toronto and did History, then Brooklyn Paramount in New York and finished at the Wiltern in L.A. We really wanted to use it as an opportunity to test the market and see what was out there on the live side, do some promo and get people buzzing.
It felt like there was so much enthusiasm from fans, especially millennials who grew up with her and Lizzy McGuire. How much of a role has nostalgia played?
There’s no question about nostalgia being a driver in the business at large these days. You see it from Deftones on the rock side of things, to Alanis Morissette or Sarah McLachlan. You see it in the pop space too.
The world's pretty complicated right now, to be kind, and I think people really long for that feeling that they had when they were kids and a little more carefree. In Hilary's case, there were some great songs and moments and fans are really celebrating that. Many are at the age where they have some disposable income and want to come out to a show.
The sales on the tour, globally, were bananas. We’re getting some really big support at radio, and that helps. It also helps that the music's great. The reviews of the album are super strong. I think it’s one of those things where people say, “Hey, have you heard the new Hilary Duff record? Really good!” You get that narrative going, which is important.
You’ve seen this kind of second act success with Mother Mother, who blew up with a new generation on TikTok well over a decade after their initial breakout. Do you feel you have lessons from working through that with them that you’re now applying with Hilary?
No question about it. Mother Mother continues to do very well. They’re on the radio in Canada and they play arenas, but I think people don't realize the extent of their global footprint.
The importance of a global footprint in your business is one of the things I think a lot of people in Canada actually don't necessarily realize. By nature, it's hard to see outside of what you see in your marketplace. Mother Mother played 90 shows just in Europe in two years. They've toured extensively in South America, Mexico, Australia, Asia. I don’t think there’s an alternative band from Canada who have done that to the extent that they have. Being able to take a band like that and plug into their network around the world, that's been a difference-maker for them.
Mother Mother played Lollapalooza in Mumbai, Berlin, Paris, all the Lollapalooza South America shows. We've been very fortunate to get a lot of support from C3 Presents [booker of Lollapalooza] and from Huston Powell who oversees all their booking globally. He’s been a fan of Mother Mother and it's really helped us open a lot of doors internationally. Most artists don't get to go to Mumbai, let alone play in front of 50,000 people. It was actually one of their favourite festival experiences of their life.
I've been fortunate to be very busy for a number of years, but this is a whole different thing. There's so much happening all at once for Hilary right now. We're very blessed for that.
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