Ranking the Worst Actors of All Time

24. Owen Wilson

Owen Wilson’s comedies seem to be very hit or miss for most people. For example, Wedding Crashers was a hit while Night at the Museum was a total bust, according to many. Others have cited their dislike of his acting style as “boring” and “unnatural,” and that his broken nose is a distraction. Not to mention, he’s apparently a total womanizer in real life. All we have to say about that is, Wow. (Sorry, we couldn’t resist throwing that in there.)

23. Vince Vaughn

Like his buddy Owen Wilson, Vince Vaughn has starred in a number of comedies over the years, with some tanking and others performing well. In movies with subpar screenplays that have tanked in the past, such as The Dilemma and The Watch, moviegoers have criticized his performance for simply resembling a shadow of his former, funnier roles. As it stands, Vaughn’s acting and comedic skills just aren’t strong enough to overcome a subpar screenplay or storyline.

22. Ryan Phillippe

In the late ’90s it felt like Ryan Phillippe was everywhere. His role as Sabastian Valmont in Cruel Intentions earned him widespread acclaim and an almost decade-long marriage to costar Reese Witherspoon. So why is it that we literally never hear about him anymore? Well, since his Cruel Intentions days he’s acted in several box office failures that blacklisted him from future big roles. But in Phillippe’s defense, he’s not actually that bad of an actor and it probably didn’t help that his then-wife’s career was really taking off at the same time that his was beginning to tank.

21. Luke Wilson

The less-famous and (arguably) less-talented brother of Owen Wilson is known for being a part of the “Frat Pack,” a group of bro-y dudes (including the Wilson brothers, Will Ferrell, Vince Vaughn, Jack Black, and Ben Stiller) who made comedy movies together in the 2000s. Some of them were genuinely good (hello, Old School and Dodgeball), while others were hard to sit through. Simply put, Luke Wilson’s acting is just boring compared to his brother’s odd and “out-there” characters.