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Ryan Reynolds has turned advertising on its head during the past three years with the launch of his creative agency Maximum Effort. So much so that when we were pitched a story about Maximum Effort being acquired by a CTV player called MNTN, we thought we were being had. Well, the news is real and it appears Reynolds has done it again after selling Aviation Gin to Diageo for a small fortune. In honor of this news, The Drum decided to celebrate Reynolds' good fortune with a look back at five of our favorite spots from adland’s favorite trickster.

Kenneth Hein, US editor: The gift that does not give back

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'Twas three weeks before Christmas and Peloton came under immense fire (well before the Tread+ recall PR fiasco) because of a tone-deaf 2019 holiday ad called ‘The gift that gives back.’ It featured a wife receiving an exercise bike from her husband and chronicled her unbridled enthusiasm about the gift. The internet had a field day and so did Ryan Reynolds’ Aviation Gin.

Seemingly instantaneously, he cast the actress from the much-maligned Peloton ad, Monica Ruiz, in a new spot for Aviation Gin, where she's pictured at a bar blowing off steam with her friends. For a full 12-second beat, no one says anything until Ruiz finally breaks the silence. “This gin is really smooth,” she says. Her friends offer encouragement and toast to “new beginnings.”

She chugs an Aviation Gin martini before her friend slides over a second cocktail to help ease her pain. Her friend chimes, “Going to be a fun night,” and caps it with the kicker: “You look great, by the way!” Reynolds tweeted out the spot with the message “exercise bike not included” #AviationGin.

And alas, we all sat around our warm holiday homes reveling at the perfectly-timed and well-executed spot.

Sam Bradley, assistant editor: Mint Mobile voicemail

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While a face that can win the hearts of a good percentage of the public is certainly an advantage in advertising, one of Reynolds' best creative pieces relies totally on his dulcet Canadian tones.

This voicemail message left for Mint Mobile customers, informing them about a data deal to help them through lockdown, features the actor and ad man opining about the ennui of the pandemic, as a customer update turns into an impromptu confessional. The ad provoked thousands of return calls to Reynolds from Mint customers, some of which were packaged together for a further response creative by the brand's team.

John McCarthy, media editor: Welcome to Wrexham

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Maximum Effort Productions — not the newly-purchased marketing agency but a sister production wing — hyped me up for the humor of Welcome To Wrexham, Reynolds' and actor friend Rob McElhenney’s efforts to improve the fortunes of a Welsh football team.

A Welsh translator absolutely roasts the pair — and they take it very well. Everything coming out of this agency is appointment viewing, whether the hardcore ad folk like to admit it or not. And I know you’re watching, because we keep writing about it. And you keep reading about it. For better or worse, this lot is almost alone in producing funny ads. Ad land, if you can be funnier, then please rise to the challenge.

Kendra Clark, US reporter: Match made in hell

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Set against Taylor Swift’s re-recorded “Love Story,” Match.com’s “Match made in hell” is a hysterically accurate rendition of how we all felt about 2020.

In the 90-second spot, Satan “matches” with a mysterious user, two-zero-two-zero, who introduces herself as “Twenty Twenty” when the two meet in thunderstorm-barraged Central Park. “So where are you from?” she coos. “Hell,” he replies. “Me, too,” she says.

The next thirty seconds offer a cinematic montage that captures the blossoming romance between the two: 2020 feeds her double-horned companion hot peppers like grapes, the two pose for selfies before a literal dumpster fire and the pair is pictured canoodling in otherwise abandoned gathering places including the gym and the movie theater. As the spot wraps, Satan muses: "I just don't want this year to end," as asteroids rain down upon a New York City skyline against a radiant pink sunset. "Who would?," says 2020, cradling her head into his shoulder. 

The campaign debuted in December of 2020 and went viral almost instantaneously. Match and Maximum Effort released a cheeky follow-up, “When Satan met 2020,” shortly thereafter. And to further capitalize on the spot’s success, Maximum Effort repurposed Satan in an April ad for Mint Mobile

Imogen Watson, senior reporter: Arlene’s big leap

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My cousin was born on a leap year and every birthday I find it funny to mis-age her. It never gets old — well, for me. So, when I saw "Arlene’s big leap," I rejoiced in the fact that I wasn’t the only one.

Meet Arlene Manko, born in 1936 on a leap year — making 2020, technically, her 21st birthday. To celebrate, Ryan Reynolds wanted to do something to celebrate the fact that at 84, she was finally of legal drinking age. Her choice of liquor? Aviation Gin of course.

Kenneth Hein, US editor: NewManageMint Powerpoint

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We would be remiss to not include this “ad” on the list. The premise is simple: Mint Mobile was meant to shoot a bit budget ad but had to switch gears because of lockdown. In its place is Reynolds conducting a clunky Powerpoint presentation.

Along the way, he checks off all of the virtual presentation cliches with which we’ve all developed a love-hate relationship. “Let’s go to screenshare.” Almost clicking the wrong file, he says, “Okay, that’s not it. Here we go.” Then there’s some cheesy graphics, meaningless pie charts and the endless array of 'thank you' slides. Plus, we get an intimate look at the folders on his desktop. They include: “Name of third daughter,” “Thoughts on time travel” and “Books to say I’ve read.” Simple and funny, it perfecelty reflected the mood of last May in a way that we that would could all relate to.