The Sweetest Moments from Celebrity Kids’ First Day of School
Whether it’s the first day of kindergarten or a tear-filled cross-country drive to college, no parent is ever truly ready for the emotional wrecking ball that is school drop-off day—and celebrities are no exception. From Usher sharing a heartfelt video cheering on his son, Cinco, at Howard University to Kevin Hart fighting back tears after dropping his daughter, Heaven, at her freshman dorm, back-to-school feelings hit everyone the same. As a new school year kicks off, we’ve gathered the most heartwarming videos and photos of celebrities dropping their kids off at school.
Usher Drops Cinco at Howard University
This summer, Usher took a break from his co-headlining stadium tour with Chris Brown to spend time with his son, Usher “Cinco” Raymond V, at Howard University’s welcome week. Sharing a clip of the milestone on TikTok, the R&B star offered heartfelt words of encouragement to his eldest son.
“This is just the beginning, man. What a wild and amazing adventure. You’re here in the Mecca. It’s your time to shine, kid. You wanted this; you manifested this; you called it into action,” he said. “You didn’t give up. Now this is your beginning, man. I’m so proud of you.”
Related: The Flyest HBCU Dorm Room Transformations on Social Media
Angelina Jolie Drops Zahara at Spelman College
In 2022, Angelina Jolie was among the proud Spelman College moms dropping off their daughters for move-in day. When asked how it felt to leave her daughter Zahara on campus, the actress shared that she was excited, but admitted she was trying to hold back tears.
Tracy McGrady Drops His Daughter Off at Tulane University
Tracy McGrady just moved his daughter Laycee into Tulane University
pic.twitter.com/G9iAY9gtU7
— ًWave Checkers (@wavecheckers) August 12, 2026
Former NBA player Tracy McGrady posed for a photo with his family after he dropped his daughter, Laycee, off at Tulane University for her freshman year.
Kevin Hart Moves Heaven Hart Into Her Freshman Dorm
Kevin Hart shared an emotional Instagram post after moving his oldest daughter, Heaven Hart, into her college dorm in 2023.
Frowning in the photo, the proud dad expressed his emotions in the caption. “I’m not crying, you’re crying…. So proud of my daughter….I can’t even say little girl anymore because you have blossomed into the most amazing young woman ever!!!!! God knows I am beyond proud of you and that I love you with my all. Fly Heav Fly….The world is yours!!!!! My baby girl is off to college…. I cried in the car!!!!”
Gizelle Bryant Drops Off Daughters Adore and Angel
“The Real Housewives of Potomac” star Gizelle Bryant had a busy summer with back-to-back college move-ins. Last summer, her daughter Adore settled into Hampton University, while her daughter Angel headed to Spelman College, and she made sure to help them both decorate their dorm rooms.
Kimora Lee Simmons and Russell Simmons Move Aoki Into Harvard
In 2019, Aoki Lee Simmons moved into Harvard University with the help of her parents, Kimora Lee Simmons and Russell Simmons. Beyond helping unpack, Kimora made sure Aoki felt comfortable straight away by inviting a group of girls from her floor out to dinner. Talk about a great way to help your kid make friends!
Barack and Michelle Obama Drop Malia Off at Harvard
When Malia Obama started at Harvard in 2017, her parents, former President Barack Obama and Michelle Obama, were there to help her settle into her dorm, just like any other parents. Later, as they departed campus, the couple sported dark sunglasses, likely hiding a few tears behind the lenses.
Barack Obama Dropping His Daughters at Elementary School
To put that emotional college send-off into perspective, former President Barack Obama was captured back in 2008 giving his young daughters, Sasha and Malia, goodbye kisses at their elementary school. How time flies!
Teyana Taylor First Day of School Photos with Daughters Iman Jr. and Rue Rose
Iman Shumpert shared photos of his ex-wife, Teyana Taylor, and their two daughters, Iman Jr. and Rue Rose, before the girls headed off to their first day of school. The young girls looked adorable and stylish, with Iman Jr. rocking a red dress, matching red-and-blue hair ribbons, and a pair of Jordans.
Michael Strahan Drops Sophia Off at Duke University
In 2023, former NFL star and TV host Michael Strahan traveled to North Carolina to drop off his youngest daughter, Sophia, at Duke University. Sharing the moment on Instagram, he wrote: “Can’t believe how time has flown by, and I’m so proud of her. I know she’s going to crush college life!! #DukeDad”
Khloé Kardashian Celebrates True Thompson’s First Day of Kindergarten
When True Thompson started kindergarten in 2023, Khloé Kardashian pulled out all the stops, celebrating the milestone with balloons and a personalized notepad-style poster. She shared the sweet moment on Instagram, writing that she was “not ok! Next, it will be prom.”
Kulture and Wave Show Off Their School Bags
Cardi B captured her kids, Kulture and Wave, posing for their first day of school in 2024. The stylish siblings proudly showed off their backpacks for the camera, with Kulture carrying a Hello Kitty bag and Wave sporting Spider-Man.
Zhuri James’ First Day Of School
In 2023, Savannah James shared a photo of her daughter Zhuri James’ first-day-of-school outfit as she entered third grade. The only daughter of the NBA’s LeBron James looked adorable in her school uniform, showing off a gorgeous silk press and a bright pink backpack.
