Frank Sinatra and Kendall Jenner: An Unlikely Link

When Old Blue Eyes Met Reality TV Royalty

Few pairings seem as unlikely on paper as Frank Sinatra, the velvet-voiced crooner of the 20th century, and Kendall Jenner, a 21st-century supermodel and reality television star. Yet the two have become linked through an advertising campaign that reworked one of Sinatra’s most beloved recordings, “My Way”, into the soundtrack for a Jenner-fronted fashion film. The connection is not biographical, nor romantic, nor familial — it is cultural, built on music, marketing and the enduring power of a 1969 anthem.

Who Was Frank Sinatra?

Frank Sinatra was an American singer, actor, and producer who lived from 1915 to 1998. Over a career spanning decades, he became one of the most influential vocalists in popular music history, celebrated for his phrasing, his swagger and his association with the “Rat Pack” era of Hollywood glamour. Among his most enduring recordings is “My Way”, an English-language adaptation of the French song “Comme d’habitude”, which Sinatra released in 1969. The track achieved modest chart success in the United States and Canada upon release, but it went on to become one of his signature songs, closely tied to his legacy as an artist whose career was, famously, done “his way”. Decades after his death, the song remains a cultural touchstone, frequently covered, remixed and referenced across film, television and advertising.

Who Is Kendall Jenner?

Kendall Jenner rose to prominence as a member of the Kardashian-Jenner family, first through reality television before building an independent career as one of the fashion industry’s most prominent models. She has walked for major international fashion houses, appeared on countless magazine covers and built a substantial following across social media platforms. Jenner has also fronted a number of high-profile advertising campaigns over the years, lending her image to beauty, fashion and sportswear brands looking to capture a younger, style-conscious audience. It was through one such campaign that her name became tied to Sinatra’s.

The Adidas Campaign That Brought Them Together

In January 2017, Adidas Originals launched a global campaign titled “Original Is Never Finished,” which reimagined the brand’s streetwear identity through a remix of Sinatra’s “My Way.” The campaign featured figures from across music, skateboarding, sport, style and art, and launched globally on 18 January 2017.

Adidas Originals, the brand’s streetwear-focused sub-label, deliberately chose to rework what was described as an “overdone track” — Sinatra’s “My Way” — and push the reinterpretation so far that it felt wholly its own. The idea was to demonstrate that true originality often arises from past influences, rather than existing in isolation from them. By the end of the campaign period, Adidas reportedly recorded a 34% increase in global sales compared with the previous campaign cycle, making it the brand’s most successful Originals push to date.

Jenner’s Role in the Campaign

Kendall Jenner starred in a later instalment of the campaign, dubbed “chapter three,” which reimagined the original award-winning film. In her segment, Jenner was styled in a manner inspired by Botticelli’s painting “The Birth of Venus,” alongside a cast that reportedly included basketball star James Harden, rapper Playboi Carti, 21 Savage and Young Thug. The advert was written by Jeph Burton and art directed by Hunter Hampton at creative agency Johannes Leonardo, with direction by Terence Neale through RSA Films.

The campaign also featured short interviews with its stars, asking each what “their way” meant to them. Jenner reportedly said she tried not to get caught up in the noise, describing herself as simply living her life, having fun, and feeling fortunate to be doing what she loves in the way she wants to do it. Her answer, brief as it was, tied neatly back to the defiant, self-determined spirit that made Sinatra’s original recording so enduring nearly fifty years earlier.

Not the Only Reworking

Jenner’s appearance was far from the only time Adidas revisited the Sinatra track for this campaign. Earlier instalments of “Original Is Never Finished” featured remixed versions of “My Way” performed or reinterpreted by artists including Snoop Dogg, Stormzy, Mabel, Dej Loaf and Dev Hynes, with each artist bringing their own scene and interpretation to the film. The campaign was later recognised within the advertising industry, with its central film going on to win accolades for its entertainment and music direction. Earlier versions of the campaign had already won the Grand Prix in Entertainment for Music at the Cannes Lions awards.

Why the Pairing Still Resonates

The link between Sinatra and Jenner illustrates something broader about how classic music continues to find new audiences through advertising and celebrity culture. Rather than fading into nostalgia, “My Way” was repositioned as a flexible anthem of individuality — one that could be reinterpreted by a hip-hop artist, a Grime musician or a supermodel alike, each claiming the song’s message of doing things on one’s own terms.

For readers encountering the connection for the first time, it is worth being clear about what the link is not: there is no evidence Sinatra and Jenner ever met, and publicly documented biographies show the Sinatra family and the Kardashian-Jenner family are entirely separate, with no familial relationship between them. Sinatra’s three children were Nancy Sinatra, Frank Sinatra Jr. and Tina Sinatra, while Jenner is the daughter of Kris Jenner and Caitlyn Jenner. The relationship between the two names is purely a product of music licensing, creative reinterpretation and the marketing instincts of a global sportswear brand looking to make an old song feel new again.

As both figures continue to feature in popular culture conversations — Sinatra through the endless rediscovery of his catalogue, and Jenner through her ongoing modelling and media career — their unlikely 2017 crossover remains a reminder of how far a single song can travel across generations, genres and industries.