Frank Sinatra and Kendall Jenner: The Story Behind the “My Way” Connection.

Introduction

Frank Sinatra and Kendall Jenner  may seem like an unlikely pair. Sinatra was one of the most influential singers and entertainers of the twentieth century, while Jenner became internationally recognised through reality television, modelling and fashion. Despite their different careers and generations, their names are connected by a memorable advertising campaign.

The link dates to 2017, when adidas Originals released the third chapter of its Original Is Never Finished campaign. The film featured Kendall Jenner alongside other contemporary cultural figures and used a reimagined version of Sinatra’s signature song, “My Way”. The campaign explored originality, creativity and the idea of giving established cultural icons a new interpretation.

According to adidas Group’s 2017 annual report, the campaign used a remix of “My Way” to connect musical history with contemporary streetwear culture.

But what exactly connects Sinatra and Jenner? Did they work together, did Jenner sing the song, or is there another story behind their names appearing together? This article separates the documented facts from assumptions and explains why the pairing remains interesting.

Quick Answer: What Connects Frank Sinatra and Kendall Jenner?

Frank Sinatra and Kendall Jenner are connected through adidas Originals’ 2017 Original Is Never Finished advertising campaign. The campaign used a reimagined version of Sinatra’s “My Way”, while Jenner appeared as one of its featured personalities.

There is no reliable public documentation establishing that they had a personal relationship, performed a duet or worked together in person. Their connection is primarily cultural and commercial: Sinatra’s music provided part of the campaign’s creative foundation, while Jenner represented a contemporary generation of fashion and entertainment.

1. Who Was Frank Sinatra?

Frank Sinatra was an American singer and actor whose career helped shape popular entertainment for generations. Born on 12 December 1915 in Hoboken, New Jersey, he became known for his distinctive voice, phrasing and expressive interpretations of popular songs.

Sinatra rose to prominence during the big-band era before establishing himself as a successful solo performer. His recordings, live performances and film appearances made him one of the most recognisable entertainers of his time.

Some of his best-known recordings include “My Way”, “Fly Me to the Moon”, “New York, New York” and “Strangers in the Night”. His interpretations often conveyed confidence, reflection and emotional intensity, helping his music remain relevant to audiences long after its original release.

Sinatra also built a substantial acting career. His film work included From Here to Eternity, for which he won the Academy Award for Best Supporting Actor, and The Manchurian Candidate. His achievements across music and film contributed to his lasting place in popular culture.

Sinatra died on 14 May 1998. Although he is no longer alive, his recordings continue to appear in films, television programmes, advertisements and other media.

This continuing cultural presence helps explain why a song associated with Sinatra could be used in a fashion campaign nearly two decades after his death.

2. Who Is Kendall Jenner?

Kendall Jenner is an American model and media personality who became widely known through the reality television series Keeping Up with the Kardashians. Born on 3 November 1995, she later developed a career in fashion, working with designers, modelling agencies and international brands.

Her professional work includes runway appearances, fashion editorials, commercial campaigns and partnerships with consumer brands. Jenner’s public profile also extends to social media, where she has built a large international audience.

Fashion advertising frequently uses recognisable personalities to communicate a brand’s identity. In Jenner’s case, her visibility across television, fashion and social media made her a prominent figure in campaigns aimed at younger audiences.

Her appearance in the adidas Originals campaign was part of this broader professional career. It placed her alongside musicians and athletes in a creative project that brought together different forms of contemporary culture.

Although Sinatra and Jenner worked in different eras, both became recognisable names beyond their primary professional fields. Sinatra’s influence extended from music into film and entertainment, while Jenner’s profile developed across modelling, television and fashion marketing.

3. How Did Frank Sinatra and Kendall Jenner Become Connected?

The connection emerged through the Original Is Never Finished campaign by adidas Originals.

The campaign explored how familiar creative works can be reinterpreted for new audiences. Rather than presenting originality as something entirely separate from the past, adidas used references to established music, art and cultural figures to show how older ideas can inspire new expressions.

Sinatra’s “My Way” played an important role in this concept. The song’s association with individuality and self-determination suited the campaign’s message about creating your own identity.

Kendall Jenner appeared in the campaign’s third chapter, released in August 2017. Contemporary coverage from The Drum described the film as a visually striking reinterpretation of art and culture, accompanied by a reworked version of “My Way”.

This is the central fact behind the pairing. Sinatra’s music was part of the soundtrack, while Jenner was one of the on-screen personalities.

The campaign did not establish that Sinatra and Jenner knew each other or collaborated directly. Instead, it brought together cultural references from different periods in a single piece of advertising.

4. What Was the adidas Originals “Original Is Never Finished” Campaign?

Original Is Never Finished was a creative campaign built around the idea that originality continues to evolve. Its films drew inspiration from music, visual art, sport and streetwear, using familiar cultural references in new ways.

The first campaign film launched in early 2017. Adidas described it in its annual report as a project featuring visionaries from music, skateboarding, sport, style and art. The film used a remix of Sinatra’s “My Way” to reinforce its message about reinterpreting the past.

The campaign later expanded with additional instalments and new casts. In August 2017, the third chapter featured Kendall Jenner alongside figures including basketball player James Harden and musicians such as 21 Savage, Young Thug and Playboi Carti.

The film incorporated surreal imagery and references to well-known artworks. These visual choices supported the campaign’s broader idea: cultural icons can be revisited and transformed rather than simply copied.

For adidas Originals, this approach helped connect its heritage products with a contemporary audience. The campaign did more than promote footwear and apparel; it also positioned the brand within wider conversations about creativity and self-expression.

You can read contemporary reporting about Jenner’s appearance in the campaign in The Drum’s coverage.

5. Why Was “My Way” Used in the Advertisement?

“My Way” is one of the songs most strongly associated with Frank Sinatra. Its themes of independence, personal choices and looking back on one’s life make it a natural fit for campaigns built around individuality.

However, the song’s history began before Sinatra’s famous recording. The English-language version was adapted by Paul Anka from the French song “Comme d’habitude”, associated with Claude François and Jacques Revaux. Sinatra recorded and popularised the English version in 1969.

Over time, “My Way” became associated with confidence, personal identity and the willingness to follow an individual path. These themes aligned with the adidas campaign’s message that originality is not fixed; it can be revisited and reinvented.

The advertisement used a reworked version of the song rather than simply relying on the emotional effect of an untouched classic. This approach connected a familiar recording with modern production and imagery.

For viewers who recognised Sinatra’s music, the soundtrack offered a reference to an earlier generation. Meanwhile, the contemporary cast and visual style made the campaign relevant to a different audience.

The combination illustrates how music can bridge generations, especially when a brand uses a familiar song to give its advertising a recognisable cultural identity.

6. Did Frank Sinatra and Kendall Jenner Ever Meet?

There is no reliable public documentation establishing that Frank Sinatra and Kendall Jenner met in person.

Their lives overlapped briefly: Jenner was born in 1995, and Sinatra died in 1998. However, the fact that both were alive during part of the same period does not demonstrate that they met or had a personal connection.

The adidas campaign that linked their names appeared in 2017, almost two decades after Sinatra’s death. Consequently, it should not be described as a direct collaboration between the two individuals.

It is important to distinguish between a shared cultural project and a personal relationship. A brand can use a recording by one artist in a campaign featuring another personality without those individuals ever meeting or working together.

In this case, the available campaign reporting supports a connection through music and advertising. Claims about a friendship, family relationship or personal encounter should not be presented as established facts without credible supporting evidence.

7. Did Kendall Jenner Sing Frank Sinatra’s “My Way”?

The documented campaign descriptions identify Kendall Jenner as one of the people featured in the advertisement. They describe the soundtrack as a reworked version or remix of Sinatra’s “My Way”.

They do not establish that Jenner sang the song or recorded a duet with Sinatra.

This distinction matters because the appearance of two celebrity names in the same campaign can easily be misunderstood. Jenner’s role was as an on-screen personality within the adidas Originals film, while Sinatra’s connection came through the music.

The campaign’s creative approach depended on combining established cultural material with contemporary figures. It did not require Jenner to perform the song herself.

Therefore, describing the advertisement as a Frank Sinatra–Kendall Jenner duet would be misleading. The more accurate explanation is that the campaign featured Jenner and used a reimagined version of a song closely associated with Sinatra.

8. What Made the Campaign Memorable?

Several elements helped the campaign stand out.

A familiar song in a new setting

“My Way” already carried decades of cultural associations. Reworking it for a fashion advertisement gave audiences something recognisable while presenting it in a different context.

A mix of generations

Sinatra’s music represented a well-established musical legacy, while Jenner and the other featured personalities reflected contemporary fashion, sport and music. The contrast helped the campaign bring different cultural periods into the same creative space.

References to art and history

The film used visual references to famous artworks and historical imagery. Rather than relying on a conventional product demonstration, it built a distinctive visual world around the concept of originality.

A clear brand message

The phrase Original Is Never Finished communicated the idea that creativity can continue to develop. By revisiting familiar music and art, the campaign illustrated its message rather than merely stating it.

The power of cultural recognition

Recognisable songs and public figures can help advertising attract attention. When audiences identify a piece of music or a personality, they may become more interested in the story behind the campaign.

Together, these elements made the advertisement an example of how brands can use music history and contemporary celebrity to communicate a broader creative idea.

9. Why Do People Search for Frank Sinatra and Kendall Jenner?

The pairing is unusual enough to raise questions. Sinatra is associated with classic American music and film, whereas Jenner is widely recognised for modelling, reality television and modern fashion culture.

Their names appear together because the adidas campaign combined Sinatra’s music with Jenner’s appearance. Someone who encounters the advertisement, a clip or a reference to “My Way” may naturally search for both names to understand the relationship.

Search engines can also surface related names together when an article, video or advertisement mentions them in the same context. That does not necessarily mean the people were personally connected.

For readers, the most useful approach is to identify the original source of the connection. In this case, contemporary campaign coverage and adidas’s own reporting provide a clear explanation.

The story is interesting precisely because it shows how cultural references travel across generations. A classic song can find a new audience when it appears in an advertisement featuring a modern public figure.

Final Thoughts

The story of Frank Sinatra and Kendall Jenner  is a clear example of how music and celebrity can connect different generations without requiring a personal relationship between the people involved.

Their documented link comes from adidas Originals’ 2017 Original Is Never Finished campaign. The advertisement featured Jenner and used a reimagined version of Sinatra’s “My Way” to communicate a message about originality, reinvention and creative identity.

There is no reliable public documentation establishing that Sinatra and Jenner met, were related or performed together. Understanding that distinction helps separate the campaign’s real history from assumptions that can arise when two famous names appear side by side.

Ultimately, the pairing demonstrates the lasting influence of Sinatra’s music and the ability of modern advertising to introduce classic cultural works to new audiences.