The top 100 defining pop culture moments of 2021

Here’s Thomas and Tranna’s mega-list of the good, the bad and the cringe from the past year

The last year has been one hell of a rollercoaster ride. Many of us spent the first quarter of it in lockdown, then life got to feel kind of normal for a bit and, now, everything is uncertain yet again. Through all the ups and downs, it’s arguably pop culture that has kept us going or, at the very least, has provided some comfort. Whether it was watching Mare of Easttown every week or debating the hotness of Pete Davidson, pop culture provided a much needed escape. 

Throughout the year, in writing this column, we’ve taken a close look at some of the most defining pop culture moments, and we couldn’t think of a better way to end the year than by making a list of the top 100 defining pop culture moments of 2021—we love a countdown! Of course the list is subjective, so don’t come for us for not including Mariah Carey’s McDonald’s holiday collab or anything related to The Real Housewives franchise (we don’t fuck with that). The list is not inherently celebratory; it’s a reflection of both the good and the bad, the inspiring and the cringe, the uplifting and the tragic. 

So without further ado, we offer you the list…   

100. Justin Bieber not wearing the merch in his TimBiebs Tim Horton’s campaign 

99. Montreal mayor, Valérie Plante, accidentally saying “penis” instead of “tennis” (we always have dick on the brain too, Val!)

98. The confusion around what an NFT really is 

97. Mitsou on Canada’s Drag Race (and Chosen Family)!

96. Keke Palmer interviewing Megan Thee Stallion at the Met Gala

95. Lizzo and Chris Evans DMing each other

94. The queer indifference to Get Back, The Beatles documentary

93. Chris Harrison getting fired from The Bachelor (buh-bye!) 

92. Rosie O’Donnell on Everything’s Iconic with Danny Pellegrino

91. Alanis Morissette denouncing the Jagged documentary

90. Addison Rae’s disastrous performance in He’s All That 


89. Charlie Puth showing off his bulge for his 30th birthday

88. The Fall of the Cuomos (Chris can still get it)

87. The hotness of John Reynolds on Search Party

86. The end of Daft Punk

85. Ann Pornel’s fashion being the true winner The Great Canadian Baking Show

84. Michael R. Jackson’s observational social media presence 

83. Michael Theo of Love on the Spectrum launching his own podcast, Mr. A+

82. Instagram’s Boss Baby Brody blowing up

81. Billie Eilish’s British Vogue cover  

80. Clara Luciani’s epic French disco album Coeur

79. Erika Casupanan becoming the first Canadian to win Survivor  

78. Dannii Minogue’s two-hour interview on the This Is Disco podcast

77. Ryan O’Connell joining the cast of the Queer as Folk reboot 

76. Michelle Branch re-recording The Spirit Room for its 20th anniversary 

75. Melanie C on Dancing with the Stars

74. The return of Avril Lavigne

73. Tori Amos releasing her best album in years, Ocean to Ocean  

72. The announcement of Harry Style’s skin care line called “Pleasing

71. Paris Hilton finding happiness and getting married

70. Rihanna being named National Hero of Barbados 

69. Lourdes Leon (Madonna’s daughter) becoming a thing

68. The Friends reunion

67. The sniffing of the jockstrap in Halston

66. Tina (the Tina Turner documentary) 

65. The Alec Baldwin shooting and Astroworld tragedies

64. Michelle Visage and Leah Remini filling in for Wendy Williams 

63. The Weeknd’s dystopian Super Bowl halftime show

62. Meghan McCain leaving The View 

61. The cancellation of DaBaby

60. Christine of Selling Sunset having a baby

59. J.Lo singing “Let’s Get Loud” at Joe Biden’s inauguration

58. “Death to all of them” (Wendy Williams’ death wish to Britney Spears’ family)

57. The outrageous and relentless transphobia of J.K. Rowling and Dave Chappelle (someone please get these two some help)

56. Glenn Close doing “Da Butt” dance at the Oscars

55. Disclosure doc getting snubbed by the Oscars

54. The Bernie Sanders at Joe Biden’s inauguration meme

53. Torrey Peters’ Detransition, Baby flipping the script on trans representation in literature

52. Kylie Minogue and Olly Alexander swapping identities in the “A Second to Midnight” video

51. Jazmine Sullivan’s Heaux Tales being named Pitchfork’s number one album of the year

50. The passing of fashion designer Virgil Abloh

49. The return and end of Pen15

48. Yuh-Jung Youn’s Oscar speech

47. The reunion of Bennifer

46. Ted Lasso’s Jason Sudeikis being an absolute daddy

45. Bimini Bon Boulash losing Drag Race UK, but becoming an instant fashion icon

44. Titane winning the Palme d’or at Cannes

43. The end of Shrill and Insecure

42. The cancellation of Armie Hammer (and us still not knowing if he’s a cannibal or not)

41. Devery Jacobs’ star-making performance in Reservation Dogs

40. Drew Barrymore and her totally bonkers turn as the new queen of daytime TV

39. The publishing of Sarah Schulman’s Let the Record Show: A Political History of ACT UP New York, 1987–1993

38. Murray Bartlett eating ass and taking a shit in a suitcase on The White Lotus

37. Shawn Mendes saying “It’s giving Cher

36. Madonna’s endless Facetuned Instagram thirst traps

35. Keanu Reeves and Carrie-Anne Moss defying age, time and space on the cover of Entertainment Weekly 

34. The James Corden Cinderella flash mob

33. Jennifer Coolidge being Jennifer Coolidge

32. The cancellation of Scott Rudin

31. Michaela Coel winning an Emmy

30. The rise and rise of Jeremy O. Harris (and Zola)  

29. Whoopi Goldberg on the cover of Variety

28. The scene in Hacks where Jean Smart shuts down an awful straight male comic

27. The crowning of Symone as America’s Next Drag Superstar

26. Kristen Stewart saying “they don’t” in the Spencer teaser trailer

25. Zendaya’s omnipresence (it’s her world, we’re just living in it)

24. Lady Gaga spending six months on her “Italian” accent for House of Gucci

23. 57-year-old Valérie Lemercier playing a 5-year-old Céline Dion (Aline Dieux)

22. Ellen DeGeneres becoming the villain and ending The Ellen Show

21. Chris Pratt’s super cringe Insta post about his wife (possibly the most unifying event of the year)

20. Dune, Dune and more Dune

19. Kate Winslet in Mare of Easttown

18. MJ Rodriguez getting nominated for an Emmy for Pose

17. The passing of bell hooks (and the overdue mainstream honouring of her work)

16. Simone Biles dropping out of the Olympics and winning our hearts forever

15. The emotional devastation of It’s A Sin

14. The Squid Game cultural takeover

13. The collective obsession with Succession (and Jeremy Strong’s New Yorker profile)

12. Sort Of (starring Bilal Baig) becoming the first Canadian series to feature a non-binary lead character

11. The passing of Stephen Sondheim

And let’s slow things down as we near the top of the list. 

10. “Were you silent, or were you silenced?” Meghan and Harry’s interview with Oprah

Oprah knows how to put on a show and she did not disappoint with the Meghan and Harry interview that we all watched because we were in lockdown and had nothing better to do. Oprah also knows how to steal the show. Her question, “Were you silent, or were you silenced?” remains the most iconic, memorable moment of that interview.  

9. “Hi, Gay.” Megan Stalter being an absolute legend 

Megan Stalter emerged as one of 2020’s essential comedians on Instagram and her role as Kayla, the worst executive assistant in show business on HBO Max’s Hacks, confirmed that we can’t get enough of her (we sang her praise for this magazine). But it’s her viral Pride month video as a confused straight “Butter Shop” spokesperson wishing viewers a good Pride month that sparked the now ubiquitous greeting “Hi, Gay.” 

8. Taylor Swift releasing a million albums 

Between Fearless (Taylor’s Version), Red (Taylor’s Version) and her two pandemic folk albums Folklore and Evermore, TS has been on a roll in the last two years, keeping fans obsessed with a trail of songs and easter eggs. The 10-minute epic “All too Well,” which tells the riveting story of a missing scarf that Taylor allegedly left at Maggie Gyllenhaal’s home when she was dating her brother Jake, re-ignited the internet’s interest in the singer. This is the Taylor we love: petty, ridiculous and the best songwriter of her generation. Fuck the patriarchy!

7. Kim and Kanye’s Split

With Kanye splitting his time between Wyoming and Calabasas and Kim’s profile arguably surpassing her husband’s (she finally passed the baby bar!), speculation about the future of America’s third most powerful couple (after Beyoncé and Jay-Z and Barack and Michelle at #1 and #2, respectively) had been keeping the internet talking for years when the two announced their divorce back in February. While Kanye has gone full-on born-again Christian and released his 10th studio album, Donda, in 2021, Kim bounced back quickly, winning the Met Gala, hosting Saturday Night Live and getting spotted on dates with Pete Davidson. Add to this Kourtney’s engagement to Travis Barker and it looks like the dolls will keep us interested even after their reality show ended this year after 20 seasons.

6. The never-ending story of Adele’s divorce 

The headline of Rolling Stone’s Adele cover story reads: “Adele’s Confessions: How She Turned Her Pain Into Her Most Honest Album Yet.” For how much longer do we need to hear about Adele’s “pain”? She’s a rich white woman who got a divorce—it wasn’t an abusive relationship, there was no adultery and no ugly custody battle. A relationship simply ended, like they do all the time to everyone. Can we please move on? (The album is very good though.) 

5. Bowen Yang queering SNL

In 2021, the queering of SNL was fully achieved when Bowen Yang showed up to the weekend update desk dressed as the iceberg that sank the Titanic! Arguably the comedy king of the queers, Yang is both earnest and hilarious, and he made history this year by being the first SNL “featured” player to get an Emmy nomination in the show’s 46-year history. From impersonating Fran Lebowitz to hanging out with Taylor Swift when she appeared on the show, Yang is living the life and we’re all rooting for him!

4. And Just Like That 

Did the world need more Sex and the City? No. Are we still going to watch these women whenever they unite, no matter how bad the franchise becomes? Yes, because Sex and the City is an institution unlike any other. It’s hard to think of another TV series over the last 20 years that has had the kind of massive cultural impact that SATC has. And that doesn’t mean it was a good show; it has aged horribly, and in many ways And Just Like That is trying to right the wrongs of the original series—namely its lack of gender, sexual and racial diversity. While it can feel heavy handed at times and can be cringey as fuck, this new chapter of the franchise feels fresh and bold in a way it hasn’t for a very long time. And who doesn’t start every sentence with “and just like that” now?  

3. The coming out of Jojo Siwa, Demi Lovato, Tommy Dorfman and everyone else 

With all the alone time we’ve had over the last two years, we’ve had the chance to examine ourselves in ways we may never have before—and that means a lot of people have come out of the closet (yay!). This past year alone saw the hugely publicized coming outs of Jojo Siwa, Tommy Dorfman  and Demi Lovato, to name but a few. For kids of the ’90s, like us, we never could have imagined a time when so many high-profile entertainers would make such public, empowered (and empowering) coming outs. To quote Céline Dion, “It’s wonderful.”  

2. Lil Nas X turning everyone on

Lap dancing for the devil, making out on stage with a male backup dancer at the BET Awards, giving us a naked jail shower choreo in the “Industry, Baby” video, selling 666 pairs of Nikes containing drops of human blood, appearing pregnant on the eve of his album release… Lil Nas X is definitely the sex siren of 2021, turning us on and making us think, while simultaneously pissing off homophobes and far-right TV commentators and politicians. Lil Nas X doesn’t only excel at grabbing headlines: he also released one of this year’s most exciting albums, his debut, Montero. Lil Nas X might be a power bottom but he dominated the airwaves and showed everyone that a gay rapper can achieve mainstream success. Honestly, “That’s What I Want.”

1. Britney freed, at long last 

The story of Britney’s conservatorship and her road to freedom was undoubtedly the biggest pop culture story of the year. For 13 years, Britney was under a conservatorship that controlled every aspect of her life. Usually a conservatorship is a last resort, put in place when someone is no longer physically or mentally able to take care of themselves, which was not the case for Britney, as evidenced by her extreme work schedule. During the 13 years of her conservatorship Britney released four studio albums, went on three world tours and did 248 shows during her wildly successful four-year Vegas residency. Britney herself equated her conservatorship with human trafficking. The #FreeBritney movement was started by Britney’s fans, who knew something wasn’t right, on social media. Eventually the movement gained mainstream recognition, leading the New York Times to produce an explosive investigative documentary, Framing Britney Spears, and its follow up, Controlling Britney Spears. The documentaries and the subsequent (massive) media coverage made the world take notice of Britney’s situation. This year, Britney was finally able to hire her own lawyer, who successfully (and swiftly) dismantled the conservatorship. The #FreeBritney movement became about so much more than just Britney herself: it shone a light on the corruption of conservatorships and the ways they can exploit the vulnerable people they’re supposed to protect, stripping them of not only their dignity but their ability to live their lives. The movement shed light on the dark tale of exploitation of women in the entertainment industry. Britney is an entertainer whose work has brought so much joy to millions of people, and we all just want to see her happy and free!

Thomas Leblanc is one half of the Montreal comedy duo Thomas and Tranna, hosts of the CBC podcast Chosen Family.

Tranna Wintour is one half of the Montreal comedy duo Thomas and Tranna, hosts of the CBC podcast Chosen Family.

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