What connects Caitlyn Jenner and Lamar Odom? In an unexpected union based on their shared backgrounds in sports and their association with the Kardashian family, the two public figures have announced their forthcoming podcast series, Keeping Up With Sports. A fitting title, don’t you think?

Joined by fellow athlete and co-host Zach Hirsch, Caitlyn and Lamar are set to debut their inaugural episode in the upcoming weeks, featuring none other than boxing icon Sugar Ray Leonard as their premiere guest.

This celeb pairing has prompted us to deep dive into the archives of memorable content pairings. From Drake and Bobbi Althoff to Amelia Dimoldenberg and Louis Theroux, read on for a round-up of some of our favourite unlikely pairing moments of the past.

But first, take a look at what we can expect from Keeping Up With Sports…

Alex Cooper sat down in her Pennsylvania childhood home to interview Zayn Malik for her wildly popular podcast, Call Her Daddy. The first time the 1D star agreed to do an interview in six years, he candidly opened up about coping with anxiety, discussed his relationship with his daughter, and cleared up rumours surrounding the infamous Yolanda Hadid situation.

In July 2023, a segment featuring rapper Drake on Bobbi Althoff’s The Really Good Podcast went viral, with its iconic bed setting and flinchingly awkward conversations. However, by August, the episode mysteriously disappeared from Bobbi’s TikTok, YouTube and Spotify platforms. Adding to the intrigue, both Bobbi and Drake appeared to have unfollowed each other on Instagram, fuelling speculation among fans regarding potential drama.

Kim Kardashian sat down on Jay Shetty’s podcast for a candid discussion on self-compassion and self-love. Kim shared insights into her journey as a celebrity and influencer, recounting how she had learned to prioritise self-care and reflecting on the challenges she’s faced as a parent of four and business owner.

Jennifer Lawrence seems to be a strong contender for the title of the most entertaining Hot Ones episode. Despite having only a few beverage options to alleviate the heat, she impressively endured all 10 wings without flinching. Her reactions were, of course, authentically JLaw, garnering nearly 9 million views in just two weeks. Her memorable appearance, complete with tears, might just top the charts as the show’s finest moment yet.

Taylor Momsen reunited with her on-screen brother Penn Badgley on Podcrushed, gifting Gossip Girl enthusiasts a sweet treat. The duo reminisced about their time on the show, delving into Taylor’s casting as Jenny Humphrey at only 12 years old, how she had to leave her middle school friends to join the franchise and the moment she realised she could finally make her own decisions.