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The 50 Greatest Pop Star Tweets of All Time - Billboard

Posted by Stephen Stevenson on May 23, 2019
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The 50 Greatest Pop Star Tweets of All Time - Billboard

Since becoming a major part of the mainstream fabric over a decade ago, Twitter has been an essential element of pop star mythology. Without it, we wouldn't know what an effective and charismatic naval commander Rihanna is when called to action, or how real Ariana Grande gets after she has no tears left to cry, or just how far down the rabbit hole Kanye West goes once you distract from his creative process. Without it, we might not have such perfect encapsulations of Lil Wayne vs. Pusha T, Drake vs. Meek Mill, or 2017 vs. James Blunt's New Music.

It's played a pivotal role in countless musical dramas and revelations big and small, and it's hard to imagine the last decade of pop without it. Nonetheless, over 12 years into Twitter's run, we haven't made much effort to really acknowledge and salute those tweets that have played a big a part in building the pop culture of the last decade-plus as most of the greatest songs and albums -- a snub that feels historically risky, given the service's ephemeral (and eminently deletable) nature. 

All the more reason, then, to take the opportunity to properly commemorate and celebrate all that Pop Star Twitter has given us to date. Here are our staff's all-time 50 favorite tweets from top 40's leading lights -- including a few marquee names of yesteryear, whose self-aware Twitter presences have given them new life. Some are brilliant insights, some are perplexing observations, and some appear to be altogether accidental, but all of them have helped shape our perceptions of the biggest artists of our time -- and remain relevant RTs to this day. 

50. 

Tweet Type: O.... K....

Quick Context: On April 30, 2018, at 11:30 AM, Shawn Mendes tweeted a most concise greeting, with no follow-up or additional explanation.

Most Brilliant Bit: Mendes rarely employs the all-caps, and it’s really the cherry on top here. 

49. 

Tweet Type: Iconic Shade 

Quick Context: After powering through the National Anthem at Super Bowl LII with the flu, P!nk had an epic clap back for a Twitter troll who criticized her performance. 

Most Brilliant Bit: P!nk cued up the ultimate “wait for it” moment, ending the tweet by telling her hater “You just suck by yourself on a dirty couch”

48. 

Tweet Type: On-Brand Self-Awareness

Quick Context: Richard Marx's signature ballad -- and one of the definitive pop-rock weepers of the late '80s -- had espoused a level of commitment that Marx, nearly 30 years later, apparently realized he wasn't really up for. 

Most Brilliant Bit: "I misspoke." You know the speak he's referring to. 

47. 

Tweet Type: Pop Stars -- Just Like Us

Quick Context: At the end of Camp Rock 2, the fictional band Connect 3 -- played by Joe and his brothers -- and the rest of their group lose to the other camp across the lake. Joe, it seems, has not let this go in the years since.

Most Brilliant Bit: When an ending doesn't go your way, naturally you complain about it on Twitter. Even if it was a decade ago.

46. 

Tweet Type: On-Brand Self-Awareness 

Quick Context: Soulja's smash hit "Crank That (Soulja Boy)" had previously spent 7 weeks at No. 1 in 2007, inspiring the "Soulja Boy" dance -- arguably the biggest dance craze associated with a hit song since "Macarena" -- and eventually, this slice of wisdom. 

Most Brilliant Bit: The utter... randomness of it. He tweeted this 11 years after "Crank That" hit No. 1 on the Billboard Hot 100 -- not on the anniversary of its release, or topping a chart, or achieving some milestone.

45. 

Tweet Type: Pop Stars -- Just Like Us

Quick Context: The whole world wanted Leonardo DiCaprio to win an Oscar in 2016 -- including Adele. The superstar singer shared this good-luck tweet hours before he would go on to collect the best actor trophy for The Revenant.

Most Brilliant Bit: Adele proves her Leo-fangirl bonafides with an excellent Titanic reference.

44. 

Tweet Type: Free Verse

Quick Context: French tweeted this fantastic line of disrespect days before using it in a freestyle allegedly aimed at Jim Jones for his treatment of Max B, known to his fans as the Wave God.

Most Brilliant Bit: The progression from typical online abbreviation -- “u” for “you” -- to something totally strange and surprising, but fitting for French.

43. 

Tweet Type: Pop Stars - Just Like Us (with a bit of Iconic Shade)

Quick Context: Radiohead's Thom Yorke tweeted a vague nugget of creative pseudo-wisdom ("Surround yourself with empty fields"); the Paramore frontwoman then imparted her own view of what it’s really like to be a professional artist.

Most Brilliant Bit: The whole thing is well-constructed, but "surrounded by men" hammers home her point.

42. 

Tweet Type: Good to Know

Quick Context: Followers demanded a mathematical explanation behind the band’s puzzling lyric “I get a thousand hugs, from 10,000 lightning bugs” (from Hot 100-topping smash "Fireflies"), so frontman Adam Young offered an unexpectedly earnest, two-paragraph answer -- which he based on ample research of firefly anatomy.

Most Brilliant Bit: The sign-off -- “Please don’t hesitate to reach out with any further questions!” -- which feels only half-joking.

41. 

Tweet Type: On-Brand Self-Awareness / Pop Stars -- Just Like Us

Quick Context: Though the DJ and producer was introduced to many in the early '10s through his EDM hits, he had previously made his name in the rock world -- the dissonance between the two sides of his artistry leading him to set the record straight about his roots for his new fans. 

Most Brilliant Bit: The all-caps "EMO.” It looks great on a t-shirt. 

40.

Tweet Type: On-Brand Self-Awareness / Pop Stars -- Just Like Us

Quick Context: After Musgraves tweeted “yeemotherfuckinhaw” in response to a favorable Apple Music chart update, an admitted Kacey hater named Denise questioned the country singer’s “vulgar” word choice.

Most Brilliant Bit: The tweet might not have resonated so intensely had it not been for another viral Denise: The previous month, conservative commentator Denise McAllister railed against The View on Twitter, prompting Meghan McCain, one of the show’s co-hosts, to respond, “you were at my wedding Denise…”

39. 

Tweet Type: Historically Relevant

Quick Context: Harry Styles tweeted these iconic lyrics, written by ex-girlfriend Taylor Swift, on his 22nd birthday.

Most Brilliant Bit: Straight, to the point, proper punctuation. Plus, a full-circle moment: The world had followed Styles and Swift's fleeting relationship, Taylor had written songs about their breakup (“Style,” “Out of the Woods”) and this tweet showed there were no hard feelings.

38. 

Tweet Type: Good to Know

Quick Context: Cardi B has has never shied away from an opportunity to overshare -- no matter how popular she becomes! 

Most Brilliant Bit: The fact that she knows she hasn’t touched beef in four days is so randomly specific. And the pondering emoji takes the tweet to a comically inquisitive level.

37. 

Tweet Type: Mad as Hell

Quick Context: Aaron Carter's pop stats (two Hot 100 hits) might not quite compare to Justin Bieber's (five Hot 100 No. 1s), but apparently the former can only take so many fan comparisons between the two before needing to point out how his hard-hatting back in the day made the latter's thriving possible. 

Most Brilliant Bit: "I'm also in construction." The construction sign emoji makes all the difference. 

36. 

Tweet Type: Pop Stars -- Just Like Us

Quick Context: Lil Jon was probably guilty of oversharing here, but who hasn't been in this predicament?

Most Brilliant Bit: The stretched-out spelling of "LIFFFEEEE!!" You can really feel his pain.

35. 

Tweet Type: Mad as Hell

Quick Context: Maroon 5 were snubbed as nominees -- and perhaps as performers/presenters/invitees -- for the 2011 MTV Video Music Awards, and whether out of retribution or a genuine protest of MTV's increasing shift away from music as its primary focus, Levine decided it was time for he and the awards show to throw down. 

Most Brilliant Bit: Probably that Maroon 5 ended up playing "Maps" and "One More Night" at the VMAs three short years later.

34. 

Tweet Type: Fair Question

Quick Context: The origin of Easter could be hard to understand if you didn’t grow up practicing Christianity, but it typically involves Jesus, a tomb and resurrection. Seems like ScHoolboy Q completely missed that lesson in Sunday School, anyway. 

Most Brilliant Bit: “EGG??” is the only word stylized in all caps, which makes Q's query all the more hilarious.

33. 

Tweet Type: Fair Question

Quick Context: Nicki Minaj asked her “barbz” what their bra size is. Then she went on to ask her male followers an analogous (?) question.

Most Brilliant Bit: The shock value: Bra sizes are pretty mainstream. Penis length… sure. But had anyone ever really thought about ball size before? Nick Minaj started the discussion.

32. 

Tweet Type: Good to Know / On-Brand Self-Awareness

Quick Context: Kenny G is one of the best-selling artists of all-time (and certainly the biggest among saxophonists, at least according to the RIAA). The when/where of this particular photo remains a mystery.

Most Brilliant Bit: Simply humoring the idea that Kenny G refuses to use his hands for anything other than playing saxophone -- even while riding a bicycle -- is hilarious, and particularly well-sold by his no-nonsense facial expression. 

31. 

Tweet Type: On-Brand Self-Awareness

Quick Context: In 2012, Cher was at a strange place in her life: working on her 25th studio album Closer to the Truth, starring in Burlesque and rapidly becoming the Queen of Twitter™. Needless to say, the pop legend was a bit confused as to where she was headed next in her already-ridiculous profession. 

Most Brilliant Bit: The missing space between "my" and "career." Not only does the lack of a space sell the star's exasperation, but it is quintessential Cher; she's too busy being iconic to care about punctuation or spelling.

30. 

Tweet Type: Historically Relevant

Quick Context: Following the release of her much-anticipated Sweetener album, Ariana Grande felt frustrated by the constraints of typical pop star rollouts -- and forecast her desire to roll out her music on her own terms and her own schedule, a prophecy fulfilled just months later with the unexpected release of new single "Thank U, Next." 

Most Brilliant Bit: The extra H's in "freshhh." She means it, man. 

29. 

Tweet Type: Twitter Vers

Quick Context: The queen of being extra trolled a before-and-after photo challenge circulating on the internet by posting two identical swimsuit pics and refusing to “acknowledge” time (!), an instantly legendary quote that users have applied to being late to work and missing deadlines.

Most Brilliant Bit: The perfectly bizarre choice of photo, in which a bikini-clad Mariah poses with an unamused puppy on some sort of indoor swing. Who’s behind the camera? Why are there balloons? None of this matters!

28. 

Tweet Type: Historically Relevant

Quick Context: After being inducted into the Songwriters Hall of Fame, Jay-Z broke his social media silence to tweet about all the rappers who’ve inspired him throughout the years. It was his way of showing love to black cultural game-changers, but he also made sure to include Mac Miller -- the only white rapper named besides Eminem.

Most Brilliant Bit: The timing is bittersweet, as it came almost a year after Miller dropped his critically acclaimed fourth album The Divine Feminine --the rapper even transformed the tweet into a poster for his house -- and after Miller’s shocking death last September, Jay-Z’s acknowledgement holds even more emotional weight.

27. 

Tweet Type: Fair Question

Quick Context: Not much context on this one. Is he serious? What prompted such a question? What if the meatball has tomato sauce on it? The question elicited thousands of replies on Twitter, until Bon Appétit came to the rescue and answered Post's question fairly succinctly.

Most Brilliant Bit: The outcry of responses, including many justifying how and why a meatball is, in fact, an fruit.

26. 

Tweet Type: Whoopsie?

Quick Context: At the veritable height of the conflict between Drake and Meek Mill -- which began on Twitter! -- Meek responded to the Toronto MC’s “Back to Back” with a single tweet: the letter Z. What did it mean? Was it a mistake? Didn't matter, because it was already the stuff of legend.

Most Brilliant Bit: Not much to explicate here. It really was just the letter Z. We’re all seeing the same thing.

25. 

Tweet Type: Mad as Hell

Quick Context: Bay Area native (and Veriest Online of turn-of-the-millennium pop stars) Steve Harwell of Smash Mouth couldn't resist dinging LeBron James in the midst of the contentious 2016 NBA Finals between his Golden State Warriors and James' Cleveland Cavaliers. When LBJ fans came back with Shrek jokes, Harwell was ready with his chart-stat comeback. 

Most Brilliant Bit: "Come on Sammy!" -- the "I'm trying Jennifer" of '90s meme-rock.

24. 

Tweet Type: Twitter Vers

Quick Context: Cyber bullying has remained a serious issue since the birth of the Internet, and mainly affects young teens as they grapple with self-esteem. But in his true sardonic fashion, Tyler, the Creator dismissed all of that and came up with a simple solution.

Most Brilliant Bit: The “Hahahahaha” dotted throughout the tweet makes you picture Tyler actually laughing his ass off while smashing his keypad -- without a single bit of punctuation in sight. 

23. 

Tweet Type: Iconic Shade

Quick Context: Frank Ocean and Chris Brown have since exchanged words and blows, but perhaps nothing was more devastating than Frank’s (since-deleted) concise response to a tweet from Brown comparing Ocean to “a young James Fauntleroy or Kevin Cossum.” A gifted writer, Ocean mimicked Brown’s phrasing for a truly perfect diss.

Most Brilliant Bit: The hairpin turn to “Ike Turner,” when the dagger really sinks in.

22. 

Tweet Type: Free Verse

Quick Context: You know, it was 2009 -- everyone was figuring out how to use this thing.

Most Brilliant Bit: The line break between “having” and “Tantric sex!” is tremendous to behold, but don’t sleep on how the body of the tweet reads even more smoothly when you read the handle first. Who “is still up having / Tantric sex!”? Diddy, that’s who.

21. 

Tweet Type:Fair Question / Pop Stars -- Just Like Us

Quick Context:Twitter was hardly an unknown social network back in 2010, but it was certainly a much more informal outlet -- a place where meticulously maintaining highly curated brands didn’t get in the way of a stray anatomical question.

Most Brilliant Bit:The choices to write out “2” and “ur” evoke both a comical urgency -- Ashanti needed to know the answer to this right away, no time to write this whole thing out -- and a vaguely poetic, Prince-like quality.

20. 

Tweet Type: O.... K....

Quick Context: The tweet itself requires no real explanation; Rihanna was using Twitter as a sounding board back in 2012, and her public rebuke of the devil was yet another thought put into words -- but this particular thought seemed to strike a chord, as it racked up hundreds of thousands of likes and retweets.

Most Brilliant Bit: The complete lack of context is what makes this tweet so beautiful. Rihanna was (and is) the queen of subtweeting, but this moment seems to bear absolutely no meaning outside of the singer simply and openly defaming Lucifer himself. 

19. 

Tweet Type: On-Brand Self-Awareness

Quick Context: At age 33, the Miami rapper received an honorary degree from local university Doral College, and made sure to throw it in the face of any of those who doubted his commitment to higher education -- #dale, indeed. 

Most Brilliant Bit: The grin. And the robe. And the finger, which you might not even notice the first ten times. 

18. 

Tweet Type: On-Brand Self-Awareness

Quick Context: Singer-songwriter James Blunt's brief reign over the Billboard Hot 100 in 2006 inspired a great deal of bile from critics and tastemakers -- the same sort who spent much of the celebrity-death-and-Donald-Trump-dominated 2016 proclaiming it the Worst Year Ever. For those folks, Blunt had some rough news about the year to come. 

Most Brilliant Bit: Maybe just the blue check mark next to James Blunt's Twitter handle -- confirming, yep, actually that James Blunt. 

17. 

Tweet Type: Iconic Shade

Quick Context: Back when he was at his Twitter-brattiest, EDM star Diplo made an ill-advised joke about starting a Kickstarter to "get Taylor Swift" -- then the recent star of the similarly questionable "Shake It Off" video -- "a booty." Lorde stuck up for her new pal by returning fire about a feature of the producer's anatomy she found similarly lacking. 

Most Brilliant Bit: Surely the "hm," predating the instantly iconic thinking-face emoji by a calendar year. 

16. 

Tweet Type: Good to Know

Quick Context: Drake's real name is Aubrey Graham.

Most Brilliant Bit: Drake recognizing Aubrey Plaza for the stunning and talented actress she is.

15. 

Tweet Type: Whoopsie

Quick Context: Hard to describe in words, this one is more of a feeling. But if you want to be clinical about it, it's a jumble of all-caps letters and numbers, with some well-placed exclamation points. It’s regularly circulated along with contemporary memes and jokes -- and proved particularly timely with the release of a certain movie trailer last year. 

Most Brilliant Bit: "AAAAAAAAAAAAAHHHHH."

14. 

Tweet Type: On-brand Self-Awareness

Quick Context: The girl group briefly popped back on Twitter to remind the internet that, no, TLC will NOT reconsider their zero tolerance policy on deadbeat dudes, detailed in their 1999 hit “No Scrubs.” Thanks for asking.

Most Brilliant Bit: The concision. What further explanation do you need?

13. 

Tweet Type: Iconic Shade / Historically Relevant

Quick Context: The beef between Pusha and Wayne can be traced back to BAPE hoodies in 2006; the war of words evolved over the years, but what set Wayne’s fingers to slam Pusha was “Exodus 23:1,” which took shots at Wayne’s YMCMB protege Drake.

Most Brilliant Bit: That it’s still up. Wayne has not attempted to alter the historical record, unlike many other pointed instances of aggressive Twitter engagement.

12. 

Tweet Type: O.... K....

Quick Context: Kanye West has gifted us with countless Twitter gems since joining the app in 2010, and his early years were definitely his greatest. This is just one example of his fascinating stream of consciousness, as he gets annoyed by a water bottle in his presence.

Most Brilliant Bit: You could almost hear Kanye’s exasperated tone as he tweets “oh great,” as if taking care of a water bottle was far too great of a task for him to be asked to take on without warning. 

11. 

Tweet Type: Fair Question

Quick Context: That's it. That's the tweet.

Most Brilliant Bit: Why Rhode Island? We'll probably never know.

10. 

Tweet Type: Iconic Shade / Historically Relevant

Quick Context: Late on a Tuesday night in the summer of 2015, Meek Mill called out his "R.I.C.O." collaborator for (allegedly!) not penning his own hits -- the oh-shit opening of an extended Twitter rant that ended up setting the most high-profile hip-hop beef of the mid-'10s in motion. 

Most Brilliant Bit: Never forget that this all started because Drake neglected to tweet an iTunes link to Dreams Worth More Than Money.

9. 

Tweet Type: Iconic Shade

Quick Context: While Madonna has historically opted for the higher road, Cher's longstanding antipathy toward Madge is the stuff of legend. And despite the fact the Madonna/Cher Stan Venn diagram has a world of overlap, there's one thing that tends to override hurt fan feelings: an appreciation for expertly delivered shade. And when Cher's fingers go online, the library is open.

Most Brilliant Bit: Even before you realize the context, seeing the words "I got a colonic" from any pop star's Twitter account is cause for celebration. Cher might not be a jazz singer, but it appears she's into scat humor.

8. 

Tweet Type: Good to Know

Quick Context: Cardi's rise to social media stardom has been one of delightfully unfiltered vulgarity, twisted with the rapper's singular sense of comedic timing. 

Most Brilliant Bit: Twitter sees a lot of Netflix and chill jokes. But this one cuts quickly to the point.

7. 

Tweet Type: Pop Stars -- Just Like Us 

Quick Context: Following Mac Miller’s death and her breakup with Pete Davidson, Grande bundled a joke, a reference to her recent No. 3 hit, and a heartfelt response to her exceedingly tumultuous year-plus into a 109-character tweet.

Most Brilliant Bit: “Bitch u thought” is very, very quotable for anyone who’s experienced heartbreak or tragedy.

6. 

Tweet Type: Iconic Shade

Quick Context: It’s hard to keep up with the celebrities that Azealia Banks has instigated beefs with, but no one was expecting her next target to be Lana Del Rey. The rapper hurled insults at the Coney Island Queen after LDR commented on a Kanye West post where he donned a MAGA hat. And Del Rey was not having any of Banks’ shit.

Most Brilliant Bit: Ending the hard-hitting tweet with “Period” -- both before and after actual periods -- is *chef's kiss* worthy.

5. 

Tweet Type: Mad as Hell / Pop Stars -- Just Like Us 

Quick Context: Look, if there was something going on in 50’s life to exacerbate his feelings toward his grandmother, we don’t know about it.

Most Brilliant Bit: Either the capitalized letter O, or the total lack of punctuation running through “I’m rich fuck this I’m going home I don’t need this shit." Man was fed up, and you could feel it.

4.

Tweet Type: O...K....

Quick Context: Kanye released this legendary invective as part of a long and much-retweeted Twitter rant about Wiz Khalifa -- though he later realized he was beefing over a misunderstanding and deleted the whole thing. 

Most Brilliant Bit: The lack of a "me" subject in "You have distracted from" -- the process that's being distracted from obviously existing far beyond Kanye. 

3. 

Tweet Type: Iconic Shade

Quick Context: On an episode of Fashion Police, Ciara complained of an incident where Rihanna had been rude to her at a party. “My bad ci, did I 4get to tip u? #howrudeofme" quipped the latter on Twitter, to which the former responded, "Trust me Rhianna u dont want to see me on or off the stage.” That just teed the Bad Gal up for her all-time most vicious dismissal -- of a pop hitmaker whose star was perhaps on the wane, while RiRi's rise continued unabated. 

Most Brilliant Bit: "That stage u speak of" is so cutting that no pop star has ever spoken of a stage again, just to be on the safe side. 

2. 

Tweet Type: Free Verse

Quick Context: In 2012, the majority of the world was aware that climate change was real -- and real dangerous; and with Gaga riding high off the previous year's Born This Way album, most pop fans were on the Germanotta train. But this Britney non sequitur, a stream of consciousness combination of two disparate concerns with a wild variance in global import, forced us to view both in the same light. In short, it's Twitter poetry.

Most Brilliant Bit: With her forward-facing public image being one of sweet, welcoming naivete, one imagines Britney asking, "Does anyone think global warming is a good thing?" not as a brutal, ironic putdown to the conservative chorus ignoring the entire scientific community, but as a friendly and presumption-free conversation opener to her fans on Twitter.

1.

Tweet Type: Twitter Vers

Quick Context: The pop star, who has long advocated for LGBTQ rights, tweeted this the day New York state legalized same-sex marriage in 2011.

Most Brilliant Bit: Gaga’s cry of victory is the opposite of a juicy subtweet: Instead of signifying some petty eye-rolling, when it’s retweeted into your timeline, its resurrector is probably celebrating a trivial but nonetheless thrilling milestone -- like Lady Gaga nabbing an Oscar for a category she was all but certain to win, or underdog Cardi B dethroning pop titan Taylor Swift on the Hot 100 back in 2017. Some celebrity tweets resurface every now and then just for a chance to gawk at an Internet relic: Haha, remember this? But like a chain letter, the legacy of this tweet keeps evolving, keeps taking on new meaning and contexts: For a fun time-waster, look at the top responses to this tweet -- most likely someone responding years later to both Gaga and whoever retweeted it -- and see if you can guess what prompted it.

The “I can’t stop crying” tweet is so enduring, in fact, that of all the immortal celebrity tweets out there, this one is probably most likely to survive the hypothetical death of Twitter itself. Should the website become uninhabitable or inspire a mass exodus, we will stick our flag into the soil of our next social media home and someone, somewhere, will declare: “I can’t stop crying. We did it kids.”

Blurbs by: Alexa Bianchi, Tatiana Cirisano, Stephen Daw, Nolan Feeney, Gab Ginsberg, Bianca Gracie, Paul Grein, Becky Kaminsky, Joe Lynch, Ross Scarano, Andrew Unterberger, Denise Warner and Xander Zellner

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