Why Hollywood Won't Cast Ryan Phillippe Anymore

Have you found yourself wondering what happened to that guy from Cruel Intentions? Well, you're probably not alone. At one time, Ryan Phillippe was everywhere. He was a rising acting talent — and definite heart throb — who was one-half of a beloved Hollywood power couple. But then, we found ourselves seeing less and less of him on the big screen. For that to happen to an actor who was once red hot is kind of surprising. So why exactly is Ryan Phillippe anything but a Hollywood staple these days?

His looks might have gotten in the way

For serious actors who happen to be really, ridiculously good looking, their faces can be more of a bane than a blessing. In Ryan Phillippe's case, his good looks meant automatic teen heartthrob status. That's great for landing roles in movies like I Know What You Did Last Summer and Cruel Intentions, and even 54, a movie that was notable for Phillippe showing off his sexy body. This is a bit unfair to Phillippe, who demonstrated that he does indeed have solid acting chops through his appearances in movies like Stop-Loss and Crash.

Despite being a dad in and his early 40s, Phillippe jokes that he still gets mistaken for someone nearly half his age — with some assuming that he's his teenage daughter's older brother rather than her father. Those baby-face looks are a blessing in some ways, but they may make it hard to land more solid roles.

He's not exactly a box office draw

Although Ryan Phillippe was hot stuff in the 90s, these days, he's not exactly a top box office draw. He was part of an all-star cast in Crash, a movie that far exceeded its estimated $6.5 million budget by earning over $54 million at the domestic box office. However, movie projects that relied on Phillippe as the lead or co-star haven't performed nearly as well. Antitrust, Stop-Loss, Flags of Our Fathers, and MacGruber were all commercial failures. And once an actor earns the label of 'box office poison,' it can be very hard to land promising movie roles.

He's no longer part of a Hollywood power couple

Making things even more awkward for Ryan Phillippe? Just as his acting career was cooling off, the career of then-wife Reese Witherspoon was starting to heat up. At about the same time Phillippe appeared in Crash, Witherspoon was collecting an Academy Award for her role as June Carter in Walk The Line. The fact that Witherspoon's career was doing considerably well while Phillippe's was beginning to stall might not have mattered too much to the public — at least while they were together.

Unfortunately for Phillippe, once he and Witherspoon called it quits, the public's interest in both him and his movies seemed to also fade. If you're thinking Phillippe and Witherspoon parted ways because his jealousy over her career...you're more than likely wrong. Phillippe himself blamed their marriage falling apart on how young they were when the two got together.

He returned to television

You may not know it, but Ryan Phillippe's acting career has its roots in television. He started off in the role of Billy Douglas on the ABC soap opera One Life To Live. He later had minor roles on other TV shows such as Matlock and Due South. Phillippe finally made the leap to the big screen via the 1995 Denzel Washington versus Gene Hackman sea thriller Crimson Tide. He made his true return to the small screen via a 2012 starring role in the FX series Damages. In the years since, he's mainly stuck to TV roles.

He suffered from depression

What fans of Ryan Phillippe may not know is that the Hollywood hunk has struggled with depression. "Depression has been a huge obstacle for me ever since I was a child," said Phillippe. "As you get older I think it decreases some, but I'm just innately kind of a sad person. I'm empathetic, and I take on the feelings of others and transpose myself into the position of others." While he admitted he found some advantages to being so sensitive, he also shared it could "also ruin your f***ing life."

He's living life as a (part-time) single dad

In the aftermath of his divorce from actress Reese Witherspoon and a breakup with model/actress Alexis Knapp, Ryan Phillippe found himself as a part-time single father helping to raise two (and possibly three) children. Phillippe is a devoted dad who managed to keep things amicable with Witherspoon for the sake of their kids. He admits that his arrangement with his ex-wife, which involve the children spending every other holiday season with one of their parents, is an odd one. However, he credits Witherspoon for working with him to keep things as "healthy as possible" for Ava and Deacon.

As for young Kailani, the daughter of his ex-girlfriend, Knapp, it's worth noting that despite giving the child his last name, no father was listed on the baby's birth certificate. A source told People that Phillippe is more than willing to step in and co-parent.

His charity work is a greater priority

It's also possible that one of the reasons Ryan Phillippe isn't too pre-occupied with Hollywood success is because he realizes there are more important things in life. For instance, helping out those in need. Phillippe admitted that during his work on the Bang-Bang Club in South Africa, he got an up-close look at the poor quality of life of the children there, which inspired him to get involved in Africa-based charities. Phillippe is also an ambassador for the Innocence Project, an organization dedicated to using DNA evidence to exonerate the wrongfully convicted.

He has a startup

Ryan Phillippe has also been busy at work on an e-commerce startup called Deedle.com. As Phillippe explained to Cosmopolitan, "The whole premise is that we are giving away incredible things for free." He added that the app, which is also free, involves playing a simple game for a chance to win items from "great companies like Xbox and Puma." It certainly sounds promising, although some are concerned about whether or not sensitive personal and financial information might be necessary in order to have a shot at cool prizes.

He's moved behind the camera

Ryan Phillippe wrote, directed, and starred in the 2012 film Catch Hell, which casts him in the role of a "washed up Hollywood actor." Even if it's just Phillippe poking fun at his less-than-stellar movie career prospects, it showed that he had the ability to put his own time and money into film projects. He was also a producer for the 2016 season finale episode the USA Network series Shooter, a show based on the novel Point of Impact and a TV version of the movie starring Mark Walhberg.

It's entirely possible that Phillippe may opt to direct, write, or produce future TV or movie projects, which might lead him away from primarily focusing on obtaining acting roles.

There's always the possibility of a comeback

The good news is that television has proved a strong comeback vehicle for Hollywood stars that have fallen from grace. As Ryan Phillippe improves his small screen portfolio, it's entirely possible he could land a role that causes a surge in popularity similar to what certain other actors have enjoyed. Even if that doesn't happen, he may find he's happy to direct and write projects — which could prove to be another vehicle for re-establishing himself in Hollywood.

The good news for long-suffering Phillippe fans is that the actor will be returning to the big screen in the thriller Wish Upon, which Variety writes is slated for a June 2017 release. Phillippe admits he hears from fans on social media wondering whatever happened to him. "I'm doing stuff! It may not be stuff that you see, but I'm doing stuff."