Gabrielle Union Looks Back at Her Most Iconic Roles

Welcome to Look Back At It, a monthly column where some of the most iconic Black actresses in Hollywood reminisce and reflect on the roles that made them stars. For this month’s installment, Gabrielle Union breaks down her career—from Bring it On and 10 Things I Hate About You to her most recent film, The Inspection.

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Not many have a filmography quite as iconic as Gabrielle Union’s. The late ‘90s and early-aughts saw her occupy a wide range of roles, from the best friend in She’s All That to the head cheerleader of the Clovers in Bring It On. So, which role does she consider to be her breakout? “Well, it depends on whose definition you’re using,” she explains over Zoom. “By white Hollywood’s standards, it was probably Isis in Bring it On, but by Black Hollywood’s standards, it would be She’s All That. I was ‘the Black girl’ on the poster. We recognize that feat.”

In the years since, Union has gone on to star in films with ensemble casts like Deliver Us From Eva, The Perfect Holiday, and Think Like a Man. And in 2014, she landed the leading role as Mary Jane Paul in BET’s drama series Being Mary Jane. Though she’s been in a slew of movies and television shows, she tells me that it’s her most recent film, The Inspection, in theaters Nov. 18, that finally made her feel like an actor and not just a performer.

Below, Union takes us through her most iconic roles to share the lessons she’s learned, fun memories from set, and the movies that changed everything.

Katie in She’s All That (1999)

“The first thing that comes to mind is my weave in this. [Laughs] I literally wrapped 10 Things I Hate About You and started She’s All That in the same week. At the time, my biggest crisis was which weave I could afford. Turns out, I couldn’t afford any, so I just blew a good chunk of my check on a ‘celebrity hairstylist’ to get me a weave and she put way too much hair on my head. But anyway, I made lifelong friends on this movie. Dulé Hill is, to this day, one of my best guy friends and this is where me and Lil’ Kim first bonded.”

Chastity in 10 Things I Hate About You (1999)

“I thought every movie was gonna be like this. We spent all day long together and because we had a couple of minors on set, we could only work eight-hour days. Everyone was favored, so no one had more or less than anyone else and all of our rooms and trailers were identical. We’d all eat together every night and we definitely found our way around Washington and indulged in all of the things that the Earth had to offer. My first order of business was getting Larisa [Oleynik] a fake ID. Her parents and Julia Styles’ parents signed them both over to me because I was the oldest. I just loved this experience and this cast. It was so innocent and fun.”

Shawnee in Love and Basketball (2000)

“I auditioned to play Sanaa’s role. I played basketball my whole life and I walked in with my actual basketball gear on. And Gina [Prince-Bythewood] said, ‘You don’t look like an athlete, but there’s another role I think you might be right for if you wanna go in the hallway and look at the sides.’ So I’m in the hallway with the sides and I was like, ‘Oh, I don’t look like an athlete by your standards, but I look like a whore.’ [Laughs] So with this one, we had a triple banger which is not the best trailer situation. Me and Boris Kodjoe shared a trailer and he was on the other side of it. So he had to play Sanaa’s love interest, but Sanaa and Omar [Epps] were an actual couple. So we were both on the outside. Neither of them really fucked with us at the time, but that’s how Boris and I became really close friends. Sanaa and I did not become friends on this. That happened later.”

Isis in Bring it On (2000)

“The first thing that comes to mind is the day after we filmed the scene where the Toros come to the gym and we confront them. My friends came down to San Diego where we were filming to hang out and we went to a park. At the park, there was a Black family reunion happening and they were having a watermelon eating contest.

I was like, ‘No! Why are they doing this?’ But they were just having the time of their lives. They didn’t care about any stereotypes. We talk about that afternoon ‘till this day. Like, ‘Why did it bother us so much that this Black family was eating watermelon?’ I’m bringing this up because in the movie, I’m such an unapologetically Black leader, but in real life it didn’t match.”

Conny in Two Can Play That Game (2001)

“They had originally offered me Vivica [A.Fox]’s role and I was like, ‘I don’t think I’m right for that. I’ll play a smaller role. But if I do take a smaller role, I need you to pay me.’ This and The Brothers, which came first, both opened at number one. And I remember Clint Culpepper [the former Head of Screen Gems] literally hand delivered a six-figure check to my door the Monday after. Studios are notorious for messing with your money and they’ll make you chase it and wait. Clint never did that. He brought me the first of a few massive checks. I was like, ‘Bitch, I made it.’”

Eva in Deliver Us From Eva (2003)

“This was when I became actual sisters with Meagan [Good] and Robinne [Lee]. Essence [Atkins] and I had been cast as sisters on an NBC pilot a year prior that didn’t go. So when this came, they were like, ‘Who would you want to play your sisters?’ I’d never been asked to contribute to a movie before and the first person I said was Essence. This was also around the time that I got married for the first time. Essence was the drill sergeant of my friend group and wrangled all my bridesmaids, and we had only really been friends for like a year. So when I see this movie poster, I think of my sisters.”

Syd in Bad Boys 2 (2003)

“This is when everything changed. This is when there was name and face recognition on an international scale. Bad Boys 2 was my first international press tour. It changed my whole life. This experience was the most fun six months ever. I was running around Miami like the Queen of Sheba. Martin [Lawrence] treated me like his little sister and took me everywhere. He was good in every hood, so I was good, too. I had a blast.”

Julia in Daddy’s Little Girls (2006)

“This was the first Tyler Perry movie that Tyler was not physically in. This is also, historically speaking, the lowest performing Tyler Perry movie. I don’t know if that’s a badge of honor or what. This was Idris [Elba]’s first role after Stringer Bell [Elba’s character in HBO’s The Wire]. He went from that to this, so he was finding [his character]. I remember on the first day, it was me, Tracee Ellis Ross, and Terri Vaughn. Something went a little left [on set] and we ended up with 11 hours to kill in the middle of a work day. And instead of being true professionals, going back to our hotel, and studying our lines, we went to the bars and did a pub crawl around Buckhead. We had the most incredible time.”

Nancy in The Perfect Holiday (2007)

“This is where I really bonded with Katt Williams and Charlie Murphy. I don’t know if Katt has ever taken an IQ test, but he’s truly one of the most intelligent people you will ever meet in life. He embraces life and lives on his own terms. I was like, ‘Oh shit, you can move through this industry while dancing to the beat of your own drum? And never really compromise?’ It taught me a valuable lesson.”

Geneva in Cadillac Records (2008)

“Cadillac Records was the first movie I was in that was directed by a woman, Darnell Martin. She was so unapologetically Black. It was kinda like the Katt Williams thing. They opened a door that I was peeking through, but was afraid to fully walk in. But in the movie, all of my scenes were with Jeffrey Wright. I had to know what it means to come with ‘it’ every day. I based my character on my mom. Not that the same exact thing happened to her, but it was about what it meant to stay and be a good woman. That then started me on a journey of embracing that ideal, and then eventually rejecting it in my own way. So this movie was very pivotal to me.”

Kristen in Think Like a Man and Think Like a Man Too (2012 and 2014)

“This was one long, fun circus with all of my friends. A lot of these people are family. Like, Kevin [Hart] did the toast at our wedding. Terrence J is my little bro. Regina [Hall] and Taraji [P. Henson] are family. We had a blast.

If we could do a third one, we would. Send us to Europe or Africa. We would do it in a heartbeat.”

Rachel in Almost Christmas (2016)

“Mo’Nique is a comedic genius and doesn’t get enough credit. With Danny Glover, we all took turns reciting his lines from The Color Purple to him. And every day he was with the shits. He was so awesome.

I really like working with my friends. I trust them. I know their work ethic. I know it’s not gonna be bullshit. So this was another Will Packer [the film’s producer] family production.”

Zoey in Cheaper by the Dozen (2022)

“I was never the person who babysat growing up because I don’t like other people’s kids. I didn’t even wanna have my own until I was well into my forties. So this movie was a challenge because I was with other people’s children. [Laughs] They have a very limited amount of time that they’re allowed to be on set and you have to try to get award-winning performances out of children. I was also an executive producer and number one on the call sheet, so it was a different experience. But it was so sweet and I love these kids and they’re all incredibly talented. When I was their age, I would’ve been screwing around, but these kids were focused.”

Inez in The Inspection (2022)

“This job changed my life. It took me from being an entertainer to being an actor who is actually willing to do the work to find the humanity in their characters versus judging their characters and acting out that judgment on screen. I went from a hurt person who hurts people to a healing person. This movie changed how I approach life. It changed how I think of myself, how I regard myself, and how I respect myself. It started me on this journey of decolonizing my mind and my spirit. I just turned 50 and my great grandma lived to be 110, so for the next 50 or 60 years, I want to live as free as possible. This movie put me on that path.”