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The Video Diaries: Drake
The life and times of 2025's triple-night Wireless headliner, as told by the videos that made him
Such is the legacy and visibility of Drake that it feels like he’s kind of always been here. While other contemporary stalwarts of rap might want to vanish for a few years before dropping a masterpiece (Kendrick) or kill their cultural impact with increasingly fascist rhetoric (you know who), you can always be safe in the knowledge that a Drizzy drop isn’t too far away. And from beefs to billion-streaming records, his career has been a patchwork of moments starting at the dawn of an era where you live and die by the internet.
But as well as the mantle of the most-memed rapper, Drake has also become synonymous with summer. Whether it’s his dancehall-inspired tracks like ‘Passionfruit’ and ‘Controlla’ or his many appearances at summertime festival Wireless, there’s something about the rapper that goes hand in hand with the smell of SPF and warm rum.
This weekend the rapper will cement his status as the king of Wireless when he headlines all three days of the festival to celebrate its 20th anniversary. And in preparation we’re looking at the key moments that scored him the hattrick as captured on camera…
2009 – Breaks through with ‘Best I Ever Had’
By 2009 Drake already had a couple of mixtapes under his belt, but it was So Far Gone, and in particular ‘Best I Ever Had’ that saw him break into the mainstream. Coming out the gate, Drake cemented himself as a lover boy, telling the ‘ladies’ in a live performance a year later: “This verse is for y’all. So I want you to feel me when I do it, and then maybe later I can feel you and we can feel each other.” Soon after that, Drake was signed to Lil Wayne’s Young Money after a bidding war and appeared on the label’s group track ‘Bedrock’ alongside an equally fresh on the scene Nicki Minaj.
2010 – First collaboration with Rihanna
If the 90s had Rachel and Ross, the 2010s had Drake and Rihanna. Granted, as far as pop culture ‘Will they won’t they’ couplings go, Drake and Riri was painted as more of a one-sided affair (with the latter famously responding to Drake’s declaration of love by dabbing, at the 2016 VMAs). But it was 2010’s ‘What My Name?’ that kicked off the pair’s string of huge hits together, with a music video seeing Drake lovelorn-ly following Rihanna round the offie as she tries to pick up a carton of milk.
2011 – Births ‘YOLO’
Now onto his second album, Drake was ready to claim his patch as a cultural phenomenon as well as a now massively successful rapper. Take Care’s track ‘The Motto’ popularised the war cry of a generation when it came to spontaneity and questionable decisions – YOLO (you only live once). That very motto took off in a big way, with people in equal parts devouring it through slogan merch and Instagram captions, and despising its ubiquity. It’s something Drake fully embraced by both trying to (unsuccessfully) trademark the term and broadcasting a public apology for popularising YOLO via his SNL appearance.
2013 – Wins Grammy for Best Rap Album
Drake scooped his first Grammy in 2013, picking up Best Rap Album for Take Care and thus starting his complex relationship with the awards. A few years later in 2019 his acceptance speech for Best Rap Song was cut off midway through an explanation about why the Grammys are irrelevant, while in 2020 he hit out at them again for snubbing fellow Canadian The Weeknd. Drake seemed to bury the hatchet in 2023 when he broke his boycott to submit his 21 Savage collaboration Her Loss for consideration, but he was at it again in 2024 claiming the Grammys “doesn’t dictate shit”. Regardless, this interview from after his 2013 win featuring his Uncle Steve and Alexa Chung is an oddly charming time capsule from Drake in what many fans consider his greatest era.
2015 – ‘Shutdown’ with Skepta
Around 2015 Drake was fully committed to becoming an honorary Brit. The lore goes that after watching Chelsea FC, picking up a first edition Winnie the Pooh book and working with London artists like Sampha and Jamie XX, Drizzy also fell in love with grime, building a particular bond with Skepta. When Skepta sampled a viral Drake vine for the start of ‘Shutdown’ in 2015, the song became a London anthem, and when Drake brought Skepta out to perform the track with him at Wireless in 2015 the crowd rightly lost it.
Drake would go on to massage his love of the scene with a surprise appearance at a tiny Section Boyz show in 2016 to perform ‘Jumpman’ fresh after his Brit Awards appearance, collaborations with Dave and Giggs, and even a executive producer credit on a relaunched Netflix version of Hackney-based drama series Top Boy. Next is surely a key to the city.
2016 – Performs with Rihanna at the BRIT Awards
He may have missed out on the International Male Solo Artist award to Justin Bieber (to this day Drake is surprisingly ungilded when it comes to Brits), but he poked his head in for the 2016 Brit Awards. And by poked his head in, we mean joined the stage as part of Rihanna’s performance for their Anti collaboration ‘Work’. It was a defining performance from two artists at the top of the game in their respective genres. Rihanna, unbeknownst to us giving us her last album in almost ten years (and counting) and Drake about to drop Views, one of his most successful albums to date.
2015 – ‘Hotline Bling‘
When we say you could probably hold an entire online conversation with someone communicating solely in Drake memes, it isn’t even an exaggeration. We’re talking nuance as well. From the emotional complexities in the canon of ‘Sad Drake’ to of course, ‘Hotline Bling’. Released as the lead single from his fourth album Views, the music video for ‘Hotline Bling’ launched a thousand memes with its pastel shades, Drizzy’s many dance moves, and particularly expressive facial impressions. Still going strong ten years on, the classic ‘does like’/’doesn’t like’ formula of the meme along with appropriate ‘Hotline Bling’ Drake faces took off around the same time he was beefing with Meek Mill about alleged ghostwriting. He’d later win two Grammys for the track, providing inspiration for meme victims and haters worldwide.
2018 – ‘Nice For What‘
Drake got the girls together for the ‘Nice For What’ music video. With the likes of mega celebrities Issa Rae, Letitia Wright, Jourdan Dunn and Olivia Wilde doing the rounds on screen, Drizzy leaned into his own version of a female empowerment anthem, empathising about when you’ve just “Gotta hit the club, gotta make that ass jump.” Continuing Drake’s insanely good run, and aided by being an absolute banger, ‘Nice For What’ wouldn’t shift from the charts, showing the power of a ladies man making a song for the ladies.
2021 – Billboard’s artist of the decade
Drake was breaking more records in 2021, with his EP Scary Hours 2 making him the first artist in history to have three songs debut in the charts at numbers one, two and three simultaneously. It was apt then, for Billboard to name him their artist of the decade. You could say what you like about Drake, but his popularity and impact was undeniable. Appearing on stage with his son Adonis, the rapper opened up about his insecurities when it came to his music and his inability to take a compliment. It was a rare moment stripped of the usual comedy or beefing Drake had come to be known for as he seemed humbled by his own achievements. Less impressed was Adonis, who threw a wobbly after having enough of hearing his dad say his thank yous.
2024 – Family Matters and *the* Kendrick beef
It might be an understatement to say that Drake left the latest iteration of his feud with Kendrick bruised, but for hip hop fans it was one of the most exciting beefs in recent history. As one fan puts it: “Kendrick got Drake to rap good again and Drake got Kendrick to drop consistently.” In his third (and best) diss track of the battle, Drake launched a 7-minute escalation complete with accusations worthy of “crisis management teams” and a music video packed with easter eggs and visual references that had fans of both rappers dissecting the layers of delicious disrespect. Drake may have spent the best part of a decade making us dance, but ‘Family Matters’ reminded us that he can do way more than that as well.
