“It’s always been a dream of mine to play such an iconic venue,” Miley wrote on social media just hours ahead of her Hollywood Bowl performance on Friday night (Oct. 16).

It was a funny reminder for longtime fans who have seen the child actor ascend to pop star heights; while Miley has been around and iconic for so many years, it’s really been the last few in which her career has been celebrated more widely.

At the 2024 Grammys, she won her first award (actually, two) for her Billboard Hot 100 No. 1 smash “Flowers,” taking home record of the year and best pop solo performance. In 2025, she joined Spotify’s exclusive Billions Club, delivering a hits-filled set in Paris to perform her biggest songs including “Wrecking Ball” and “The Climb.” And earlier this year, she celebrated the 25th anniversary of Hannah Montana with a Disney+ special and rare media blitz.

Already this year, she dropped Cyrus from her stage name — joining mononymous legends like Madonna, Cher and Beyoncé. And now, in her own words, she is living out a longtime dream of playing Los Angeles’ famed venue the Bowl.

Miley last performed a full set four years ago, in Mexico for over 150,000 fans (the Bowl’s capacity is 17,500). Since, she became a frequent guest at Chateau Marmont for intimate, invite-only sets but has otherwise remained absent from the stage. Needless to say, anticipation and fervor was at an all-time high for her first of two sold-out Bowl shows (the second is Sunday, Oct. 18).

From the live debut of Bass Persuades standouts to the sing-alongs for generational hits like “We Can’t Stop,” “Party in the U.S.A” and “The Climb,” here are the seven most notable moments from Miley’s major live return.