Martha Stewart explains her friendship with Snoop Dogg - what are some other multi-generational friendships?

Martha Stewart, take a bow; not content with some of the best homemaking ideas and also having legit street credibility having served time (white collar crime admittedly), the 81 year old has become the oldest swimsuit model to appear in Sport Illustrated's long hallowed swimsuit edition. The annual edition, which first saw the light of day in 1964, has traditionally sold over 1 million copies per year, with an estimated $1 billion USD made from the stand alone editions alone. 

Martha Stewart modelling is not quite as recent as people may give her credit for - since 2020, the American homemaker has been posting candid pictures of herself on her social media, earning a small army of fans who have admitted to her having an aptitude (and body of course) for modelling despite her age. It would appear that Sports Illustrated have noticed the noise being made since Stewart’s side hustle with modelling.

One of those celebrating her inclusion today is one of her closest friends - Snoop Dogg. Their unusual yet endearing friendship has been going for 15 years, when Snoop Dogg appeared on an episode of The Martha Stewart Show and since then the pair have gone on to work together as roasters on Comedy Central's 2015 Justin Bieber Roast, co-hosts of the 2021 and 2022 Puppy Bowls and co stars in various Sketchers commercials. They've also teamed up to co-host a VH1 celebrity cooking show, Martha & Snoop's Potluck Dinner Party, and judge a Halloween food competition, Snoop and Martha's Very Tasty Halloween.

"When you work with someone like Snoop, it's like having a sidekick. How great it is," Stewart had previously told People Magazine. "That's why all the comedians have sidekicks and bands because it loosens them up and lets them be freer. Snoop is my freedom." While for Snoop, he considers Martha a “homegirl” and that they "have a special bond that goes way back." That includes Martha penning the forward to Snoop Dogg’s book, From Crook to Cook: Platinum Recipes From Tha Boss Dogg's Kitchen, and Martha accidentally getting a contact high while being near Snoop Dogg - though she didn’t seem to mind when talking about the incident on Late Night with Seth Meyers.

Such an endearing friendship between two people with quite the age gap between them (Martha being 81, Snoop being 51), Peopleworld were curious what other friendships in the celebrity world also have a large age difference between the pair. Were you aware of any of these friendships or were you as surprised as you were learning how close Martha and Snoop are?

Lady Gaga and Tony Bennett (60 year age gap)

The oldest friendship on our list, the friendship between legendary singer Tony Bennett and crown princess of pop (until Madonna calls time) Lady Gaga blossomed while working together on their collaborative jazz album, "Cheek to Cheek," released in 2014. Gaga has often expressed her admiration for Bennett's talent and the impact he has had on her career. In interviews, both artists have praised each other's artistry and have spoken about the mutual respect and friendship they share. 

Their performances together and public appearances have showcased their warm rapport and genuine affection for one another, which hasn’t gone unnoticed by the public and media.

Harry Styles and Stevie Nicks (46 year age gap)

Stevie Nicks and Harry Styles have been friends since 2017, as the “Edge of Seventeen” singer appeared as a surprise guest during his first performances as a solo musician at Los Angeles venue The Troubadour. Since then, the two musicians have spoken highly of each other and have been seen supporting one another's work. 

Styles has credited Nicks as one of his musical idols and has expressed his gratitude for her mentorship. Nicks, on the other hand, has praised Styles' talent and described him as a kindred spirit. Such has been the closeness of the relationship, that when Nicks was inducted into the Rock & Roll Hall of Fame in 2019, it was Styles who inducted her at the ceremony.

Bette Midler and 50 Cent (30 year age gap)

Who knew that you could have a disagreement on the internet and it wouldn’t become a beef - that is the situation 50 Cent found himself with, of all people, Bette Midler. 

It started when Midler playfully criticised 50 Cent's support for former President Donald Trump. Instead of escalating tensions, they engaged in a friendly exchange, eventually leading to a mutual respect and friendship. Midler later shared that they had spoken privately, addressing their political differences and finding common ground. 

Midler has previously hinted at a potential musical duet between the two and described their relationship (via XXL) as being between "little Jewish lady and the great big rapper." She added, "He's such a doll ... I love him. He's gorgeous," 

Dame Helen Mirren and Vin Diesel (22 year age gap)

Apparently, Dame Helen Mirren is all about family; the actress joined the Fast and Furious franchise in 2017 and since then the actress has spoken fondly about working with Vin Diesel. The two actors have expressed their fondness for each other in interviews, with Mirren praising Diesel's professionalism and kindness, while Diesel has spoken about the privilege of working with an actress of Mirren's calibre. Their camaraderie and playful dynamic have been evident during promotional events and interviews related to the movie - the flirt Dame Helen is…

Drake and Millie Bobby Brown (18 year age gap)

Drake and Millie Bobby Brown first became friends in 2017 when they met backstage at a Drake concert. Brown has spoken openly about her friendship with Drake, considering him a close mentor and confidant. In interviews, she has described him as a supportive figure in her life, offering advice on various topics, including dating and fame. 

Drake has also praised Brown's talent and maturity beyond her years. Their friendship has faced some scrutiny due to the age difference, but both individuals have consistently emphasised that their bond is rooted in friendship and mentorship rather than anything romantic.