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In a crossover of fashion and reality TV royalty, Kendall Jenner and Anwar Hadid were spotted getting cozy back in 2018. While their romance was brief, it connected two of the most famous families in the business. Before they became the superstars they are today, Jaden Smith and Kylie Jenner were teenage sweethearts who ran in the same Calabasas circles. The relationship made perfect sense, linking the uber-famous Smith family with the burgeoning Kardashian-Jenner empire. Sofia Richie found her happily ever after with music executive Elliot Grainge, culminating in a lavish wedding that took over social media. The daughter of music legend Lionel Richie married the son of Universal Music Group CEO Lucian Grainge, keeping it all in the industry. In one of the most talked-about unions of the decade, Brooklyn Beckham and Nicola Peltz tied the knot in a massive, star-studded wedding, merging the son of David and Victoria Beckham with the daughter of billionaire Nelson Peltz. For a time, Lily-Rose Depp and Timothée Chalamet were the undisputed king and queen of the indie-cool young Hollywood couple. The daughter of Johnny Depp and the grandson of screenwriter Harold Flender created a media frenzy with their chic, high-fashion romance. This pairing created a true music industry power couple, as Evan Ross and Ashlee Simpson have been happily married for years. Their union brought together two iconic families, with the son of the one-and-only Diana Ross marrying the daughter of music manager Joe Simpson. Before they married other people, producer Mark Ronson and actress Rashida Jones were engaged in the early 2000s. It was a serious meeting of creative legacies, as the stepson of Foreigner's Mick Jones was set to marry the daughter of music giant Quincy Jones. As key members of the Calabasas social circle, it was almost inevitable that Jaden Smith and Sofia Richie would be linked together. The son of Will and Jada Pinkett Smith and the daughter of Lionel Richie have been friends since childhood and had a brief romantic fling. Before they became the media moguls they are today, Kim Kardashian and Nick Cannon were a hot couple in the mid-2000s. It's a true throwback pairing, with the daughter of famous O.J. Simpson lawyer Robert Kardashian dating the actor and son of televangelist James Cannon. In one of the most powerful and intriguing pairings of the early 2000s, Hollywood royalty married rock and roll royalty. Nicolas Cage, a member of the famous Coppola family, was briefly married to Lisa Marie Presley, the only daughter of the King, Elvis Presley. Before she became a household name, Fifty Shades star Dakota Johnson was in a long-term relationship with actor Jordan Masterson. Her lineage is pure Hollywood as the daughter of Don Johnson and Melanie Griffith. In a pairing that bridged the worlds of technology and legendary music, Phoebe Gates and Arthur Donald were a notable young couple until their split in September 2025. The daughter of Microsoft co-founder Bill Gates was linked to the grandson of music icon Sir Paul McCartney, creating a star-studded dynasty. It doesn't get more classic rock royalty than the marriage of Trevor "Trev" Lukather and Madison Cain. The son of Toto's iconic guitarist, Steve Lukather, tied the knot with the daughter of Journey's legendary keyboardist, Jonathan Cain, creating the ultimate rock and roll union.
