If they built a Hall of Fame for underachieving Hollywood actors, there would be a statue of Cuba Gooding Jr. out front wearing a #85 Rod Tidwell jersey. After his Academy Award winning turn in Jerry Maguire, Cuba has had a run of stink-bombs for the ages. From Snow Dogs to Radio, Cuba is the Da Vinci of wasted talent. Boat Trip is his Mona Lisa.

But in spite of Cuba’s prodigious underachievements, he does not stand alone. Hollywood is filled with actors and actresses committed to frittering away massive potential with poor choices of roles, miserable decisions in their personal lives and other career threatening blunders. Below you’ll find 10 of the most extreme underachievers working today:

10. Lindsay Lohan
This is a controversial pick, I realize, but I’m adamant that LiLo was on track for a promising career after standout roles in Freaky Friday and Mean Girls. Then Wilmer Valderrama got his hands on her, she was introduced to crazy uncle cocaine, and the rest is history. I ran this theory past my wife and she told me, rather cryptically, that “Lindsay Lohan could have only ever been exactly what she is.” Touché.

Her Jerry Maguire: The Parent Trap
Her Boat Trip: Labor Pains

9. Giovanni Ribisi
You may not think of Giovanni as an underachiever, but consider the following:
And that’s before we even mention that they’ve both “gone full retard” (What’s Eating Gilbert Grape/The Other Sister), or that Leo starred in a movie with Giovanni’s sister Marissa (Don’s Plum). Ten years ago they seemed like two of the brightest talents of their generation, and yet today one’s racking up Oscar nominations while the other’s doing guest spots on My Name is Earl. How is this possible? I’m not at liberty to say, but it involves the wish machine from Big.

His Jerry Maguire: Lost in Translation
His Boat Trip: Guest appearance on My Name is Earl

8. Cameron Diaz
Cameron Diaz is a physical underachiever, the female equivalent to Vince Vaughn. Lots of young actresses struggle when they have to make the leap from “teen star” to “grown-up actress” (see Lohan, Lindsay, above). Cameron Diaz is the only actress that has been forced to make the jump from “gorgeous starlet” to “looks like a baby dinosaur.” If I could go back in time and put money on the mega-babe from The Mask getting dumped by the baby-faced nerd from *NSYNC, I’d be richer than alternate-universe Biff in Back to the Future II.

Her Jerry Maguire: The Mask
Her Boat Trip: Jurassic Park

7. Luke Wilson
There is probably a case to be made that Luke is actually an overachiever, considering his complete lack of any discernable acting abilities. But on the strength of his brick-jawed good-looks and family connections you’d think he could avoid straight-to-DVD dreck like the Jessica Simpson vehicle Blonde Ambition.

And lest we forget his work in the Charlie’s Angels franchise (co-starring Cameron Diaz), the Legally Blonde franchise (with Reese Witherspoon) or My Super Ex-Girlfriend (with Uma Thurman). Luke’s criteria for picking projects appears to be:

1. The film must have a hot blonde in it.
2. The film must suck.

His Jerry Maguire: The Royal Tenenbaums
His Boat Trip: Jessica Simpson

6. Keri Russell/Claire Danes
These two highlight the “Female Fans Forever” wing in our Underachieving Hall of Fame, for their respective roles as Felicity on Felicity and Angela on My So Called Life. Despite the fact that neither one has come within a mile of their breakout role, they both enjoy saintly status among women age 25 to 35. Claire Danes even tested the irrational loyalty of her fanbase by hooking up with Billy Crudup while his girlfriend was seven months pregnant. Unfazed, her fans continue to adore her, while everyone else continues to not care.

Their Jerry Maguires: Felicity/MSCL
Their Boat Trips: The voice of Wonder Woman/Billy Crudup

5. Ed Norton
Ed just keeps piling the "under" (Death to Smoochy, The Incredible Hulk) on his increasingly dated "acheiver" status (American History X, Fight Club). Sure, he’s done some nice work in the past, but that’s like saying O.J. Simpson played some great football games. Okay, maybe The Incredible Hulk wasn’t as bad as the murder of two human beings, but my point stands.

O.J’s Jerry Maguire: USC vs. UCLA – November 18, 1967
O.J’s Boat Trip: Yeah. Let’s just move on.

4. Elizabeth Berkley
Actually, I suppose Berkley doesn’t count, considering she hasn’t so much “underachieved” as much as she “took a semi-promising acting career out behind the woodshed and put a .22 slug in its head.”

4. Christian Slater
This guy’s been on a slow and steady decline since his success in the early 90s (Pump Up the Volume, True Romance), his latest indignity coming with the cancellation of his TV series My Own Worst Enemy last year.

Why the downward spiral of a once promising career? It could be his uncanny likeness to Jack Nicholson, and that Hollywood just isn’t big enough for the both of them. Or I guess it could be his fondness of cocaine and strippers, and frequent run-ins with the law for assault, battery, driving under the influence, 3rd degree sexual assault, kicking a police officer down a flight of stairs and trying to bring a handgun onto an airplane.

Nah, it’s the Nicholson thing. For sure.

His Jerry Maguire: Gleaming the Cube
His Boat Trip: Guest appearance on My Name is Earl

3. Winona Ryder
When you’ve been in Beetlejuice, Heathers, Edward Scissorhands, Dracula and Reality Bites, and yet most people know you as, “that weird klepto chick who stole hair clips from Saks,” it might be time to fire your publicist. Just saying.

Her Jerry Maguire: Heathers
Her Boat Trip: Mr. Deeds

2. Jonathan Rhys Meyers
This guy’s career is like a super-depressing episode of Entourage:

Drama: Whoa! Why so down baby bro?
JRM: Woody Allen won’t return my calls.
Drama: But he loved you in Match Point!
JRM: Sure, but he didn’t love me in rehab.
E: Maybe you should start reading for supporting roles?
Drama: Baby bro won a Golden Globe, E, he is a leading man through and through.
E: Fine, then how about a lead role on TV? The Tudors made us an offer.
Drama: TV’s for losers, E.
E: Yeah, that’s why you’re on it!
(pause)
JRM: Turtle’s dead.

His Jerry Maguire: Elvis
His Boat Trip: August Rush

Underacheiving Fun Fact: JRM shared the screen with fellow underachiever Keri Russell in 2007’s August Rush. The film had an estimated budget of $30 million and took in just $9 million its opening weekend. That there’s some goooood casting!

1. Brittany Murphy
More interesting than Brittany Murphy’s complete career implosion following 2003’s Just Married is the role that Ashton Kutcher played in her demise. Consider the following Kutcher films and co-stars:

Just Married – Brittany Murphy
My Boss’s Daughter – Tara Reid
The Butterfly Effect – Amy Smart

Ashton’s criteria for picking projects appear to be:
1. The film must have a hot blonde in it.
2. Her career must end.

Her Jerry Maguire: Clueless
Her Boat Trip: The Wretched Curse of Reputed Warlock Ashton Kutcher