Funniest, Wildest & Messiest BOSSIP Headlines Of 2025
‘Say, Drake,’ Schemes That Todd Set Up & ‘SINNERS’: Funniest, Wildest & Messiest BOSSIP Headlines Of 2025
2025 was another hilariously messy mishmash of mayhem that peaked with Kendrick giving Drake one final WOP WOP WOPPING during his legendary performance at the Super Bowl.
In one of the buzziest Super Bowl shows ever, the Compton rapper diabolically demolished what was left of Drake during his world-stopping performance at Super Bowl LIX.
As expected, Kendrick gave the people what they wanted and performed his Grammy-winning Drake diss, “Not Like Us,” that shattered the whole entire internet.
At one point, he went full villain in a now-legendary Super Bowl moment, rapping “Say Drake…I heard you like ’em young,” while smiling deviously into the camera.
Overall, 2025 was a delicious mess fest that also gave us Diddy’s reckoning courtesy of his arch nemesis 50 Cent, Drake collecting one L after another after multiple failed lawsuits, Cardi gallivanting around with her baller boo thang Stefon Diggs, yappin’ Young Thug going viral for his now-infamous leaked chatty patty sessions in jail, and much more.
Back in September 2025, social media spiraled into chaos over countless jail calls where the “Lifestyle” rapper vented about various hot topics like his relationship with ex-BFF Gunna, his very unpopular view on serving life in prison (“If we go to life for prison, whoopty doo!”), and more in unintentionally hilarious soundbites currently making their rounds across the internet.
Check out the full episode below:
This comes after the “Money On Money” rapper lashed out at everyone from Drake to Kendrick Lamar to Andre 3000, former BFF Gunna, and GloRilla, who was allegedly called “ugly” and disrespected for her looks during a messy conversation with his boo thang, Mariah the Scientist.
Oh baby, it was quite the (hilarious) saga that will certainly be remembered beyond 2025.
What was your fave f headline of 2025? Tell us down below and enjoy ALL of the BEST BOSSIP headlines of the year on the flip.
