Skip Nav

Miley Cyrus and Emily Osment Reunite on Instagram Live Video

Miley Cyrus and Emily Osment Reunite to Roast Their Old Hannah Montana Photos

Miley Cyrus has been serving up heaps of 2000s nostalgia with her new Instagram Live series, Bright Minded, and we're beyond grateful for the trips down memory lane. Just a few days after bringing fellow Disney Channel alum Demi Lovato on for a guest appearance, the 27-year-old planned "the reunion of the decade" with Hannah Montana costar Emily Osment, who played Lilly Truscott on the series.

"This was the year Hannah was trying to make tutus and peplums happen, which should never happen."

In the sixth episode of Cyrus's ongoing livestream series, the longtime pals virtually hung out and relived "some pretty embarrassing pictures" from their Disney Channel days. After mutually cringing at the first photo — which showed Lilly's alter ego, Lola, sanitising Hannah's hands — Osment admitted, "I'm having a hard time remembering what year that was or what was happening." Cyrus remembered clearly though, replying, "This was the year Hannah was trying to make tutus and peplums happen, which should never happen." Hah! Then Osment added, "I was wearing a lot of vests." Those were the days.

HANNAH MONTANA, (from left): Emily Osment, Miley Cyrus, 'Hannah Montana To The Principal's Office', (Season 4, aired July 18, 2010), 2006-. photo: Jaimie Trueblood /  Disney Channel / Courtesy Everett Collection

The on- and offscreen friends also threw things back to their first day of doing press for the show. Cyrus hilariously reminisced, "My teeth had pretty much all decided to fall out . . . my mom had to get me some fake teeth." The big day also involved some pretty interesting outfits for the both of them — Cyrus wore a powder-blue cropped sweater vest of sorts, while Osment rocked what she described as "an Ann Taylor top." Cyrus confessed, "We look like we're going to church. I don't know who told us that this was gonna be the look for press."

Cyrus and Osment also went on to discuss the importance of stepping up to foster and adopt pets in the midst of the coronavirus pandemic. Watch Cyrus's entire Bright Minded episode above, and fast forward to about 38:50 to hear her and Osment look back on their Hannah Montana days.

Miley Cyrus and Emily Osment Reunite to Roast Their Old Hannah Montana Photos  originally posted on POPSUGAR Entertainment
Image Source: Everett Collection
From Our Partners
The 10 Most Memorable Moments in Olympic Women's Gymnastics
The Lord of the Rings Cast Reunion With Josh Gad | Video
20-Minute Disney Channel-Inspired HIIT Workout Video
Here's Where You Can Stream the Harry Potter Movies Online
Splash Cast Reunion With Tom Hanks and Daryl Hannah | Video
John Krasinski and Rainn Wilson Talk About The Office Video
Gossip Girl Style Lessons
Michael Jordan's Best Golf Outfits
Michael Jordan's Best Outfits in the '90s
Are Michael Jordan and Scottie Pippen Friends?
Are Michael Jordan and Dennis Rodman Friends?
Miley Cyrus's Black "Quarantini" Bikini on TikTok
Latest Celebrity
All the Latest From Ryan Reynolds