Were Things Really That Casual Between Drew Barrymore And Luke Wilson?

Drew Barrymore recently revealed some surprising information about her former boyfriend, Luke Wilson.

During a conversation with fellow actress Kate Hudson on The Drew Barrymore Show, the actress from Charlie’s Angels confessed that she and Wilson had an open relationship in the 1990s.

On the evening episode of her talk show on Thursday, Barrymore reminisced about her initial encounter with Wilson, stating:

“When we first met, we were young and carefree.”

Hudson, a long-time friend of Barrymore’s, provided additional details, informing the audience that they all met at the Chez Jay’s restaurant in Santa Monica.

“I was seeing him, but I think he was also seeing other people. It was an open relationship. We were young,” revealed Barrymore.

Hudson, who had a recurring romantic relationship with Owen Wilson, chimed in with “I’ve been there with a Wilson too!”

Even though all four of them have moved on over the years, fans were intrigued to hear details about the romantic experiences of some of the most prominent Hollywood stars of the 90s.

Who Is Luke Wilson?

While many individuals recognize Wilson as Emmett Richmond, the kind junior partner of one of Elle Woods’ law professors in Legally Blonde, Wilson has an extensive career in film.

The youngest of the three Wilson brothers, Luke Wilson discovered a passion for acting while studying in Los Angeles.

His career commenced when he was cast in the leading role of a short film named Bottle Rocket in 1994, written by his brother Owen and future frequent collaborator Wes Anderson.

The short film was expanded into a full-length movie in 1996, with the brothers reprising their roles. Although the film struggled at the box office, it brought Anderson widespread attention, and esteemed director Martin Scorsese has deemed it one of his favorites.

Following the move to Hollywood of the Wilson brothers, Luke was cast in Telling Lies in America, and even made a cameo in Scream 2.

Seeking to diversify his skill set and avoid being typecast, Wilson agreed to star in the romantic comedy Best Men, alongside Drew Barrymore – one of the most sought-after leading actresses in Hollywood during the decade.

He reunited with Anderson for Rushmore, portraying the boyfriend of schoolteacher Rosemary Cross.

In a feature in The Washington Post, Wilson is described as “forever the baby bro”, seen as a step below his older brothers both on and off the screen.

During the early 2000s, he was recognized as the sweet but perplexed boyfriend in numerous romantic comedies of the era and was in pursuit of a role to break free from that stereotype.

His appearance in Anderson’s The Royal Tenenbaums marked a turning point for Wilson, demonstrating impeccable comedic timing and genuine moments within the constraints of Anderson’s concise script.

Director Ivan Reitman praised Wilson, stating:

“I always had the feeling that he’s an underutilized, undervalued talent. I think it’s simply because of his good looks that he’s often cast as ‘the guy’ in many romantic films, where he’s the more straight-laced character to the colorful, eccentric female lead. I wanted to give him the chance to shine a bit more in a comedy. He’s the real deal, he’s certainly as comical as his brother Owen. His comedic skills truly come from the same DNA.”

His Collaborative Venture With Wes Anderson 

Following the twentieth anniversary of The Royal Tenenbaums, Wilson discussed his association with Anderson over the years, expressing his eagerness to reunite after their partnership endured a series of breaks.

Wilson also has concepts for their forthcoming project, sharing with The Playlist:

“We’ve discussed the possibility of creating a western with the old group over the years. So, that would be truly incredible. And I’d be just as excited as anyone else – to witness Wes’ interpretation of a Western would be incredible.”

He and Owen have also been crafting and developing a biopic about the Wright Brothers, aiming to kick-start that project in the near future.

Luke Wilson, Always a Bachelor

Wilson is renowned as one of Hollywood’s most legendary bachelors, and fans are inquiring about whether the star has intentions to settle down.

Recently, Wilson expressed his aspiration to become a father after being the fun uncle to Andrew and Owen’s children over the years.

In an interview with Hollywood Life, Wilson declared:

“I definitely want to start a family. I adore my niece and my nephews. And I am aware of how much my dad cherished being a father; that was one  of the things that brought him the most joy, so yeah, I’m 47, I’m prepared for that. I need to get to work.”

Although Wilson may desire children, he has not been in a serious relationship since 2014.

While his relationship with Barrymore purportedly appeared more laid-back than it was, it garnered considerable attention from the media at that time.

The duo were in a relationship from 1997 to 1999, when they announced their amicable separation.

Both demonstrated that there was no hostility between them, with Barrymore urging producers to cast Wilson alongside her, Charlize Theron, and Lucy Liu in Charlie’s Angels the year following their breakup.

Even today, it appears that Barrymore will never hold any animosity towards her ex, as she expressed to Hudson:

“We were just young. We were having fun. We were all playing, acting, hanging out,” she reminisced. “You’re not taking it all so seriously, and it was fun, and we had the best time.”

Subsequently, he dated Gwenyth Paltrow for about a year and later quipped to Conan O’Brien that he had a tendency to develop feelings for his female costars in every project.

To the best of public knowledge, Wilson’s longest relationship was with former American basketball player Meg Simpson. 

The pair were together from 2008 until 2014, marking this six-year relationship as Wilson’s most substantial since Barrymore.

Wilson, who turned 50 last September, has confessed that he is beginning to feel uneasy about his age, sharing with People:

“Thirty didn’t concern me. Forty didn’t concern me. I just took them in stride, but 50. I don’t know if it’s affecting me because I wake up sore in the middle of the night, and I forget the names of people I know.”

“I’m definitely starting to feel anxious about certain things,” he added.

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