10 Ugliest Free Throws in History

If you ask anybody other than Shaquille O’Neal or DeAndre Jordan, free throws are supposed to be easy.

You get a wide-open shot from 15 feet away, and as long as you hit 70% of these shots, nobody will harass you about it.

Given these conditions, most players are pretty accurate on free throws. And even when they’re not, they at least manage to draw rim during a miss.

However, some players have missed free throws so badly that their fails have gone down in history.

That said, let’s look at 10 of the most-embarrassing free throws in history.

1. Shanteona Keys Falls 10 Feet Short

Unlike most players on this list, Shanteona Keys, a 5’8″ guard from Georgia College, isn’t a bad free throw shooter. In fact, she’s really good, shooting 81.5% from the line.

But this shot was so bad that she lands No. 1 on our list. Keys had a pretty good explanation for why she looked like a 2-year-old shooting a three-pointer, telling Deadspin that her fingernail got caught in her nose on the way up.

2. Brian Okam Falls 8 Free Short

Brian Okam, a 7-footer who played for Appalachian State, didn’t fare much better than Keys during a free throw attempt, falling about 8 feet short.

In Okam’s case, he shot a moon ball that went higher in the air than it did closer to the rim. The Nigerian center never got much playing time for the Mountaineers, and we can see why.

3. DeSagana Diop Misses the Rim by a Few Feet

Despite being picked No. 8 overall by the Cleveland Cavaliers in 2001, DeSagana Diop never lived up to his potential, averaging 2.0 PPG and 3.7 RPG over 12 seasons.

His free throw shooting certainly didn’t help since he hit just 46.7% from the line over his career. Here’s a sample of how bad his shooting could get.

4. DeAndre Jordan Airballs 2 Free Throws in a Row

As great a rebounder and shot blocker as DeAndre Jordan is, it’s a shame that he’s perhaps best known for his atrocious free throw shooting.

A career 42.5% shooter from the line, Jordan has had some ugly moments. One of these includes airballing back-to-back free throws.

5. Chuck Hayes Puts a Hitch in It

Chuck Hayes shot 62.0% from the line in his career, which isn’t terrible. But on one off night against the Denver Nuggets, the Houston Rockets forward had the ugliest-looking free throw form that you’ll ever see.

6. Blake Griffin Airballs 2 Straight Free Throws

Bad free throw shooting must be contagious on the Clippers. Jordan’s teammate, Blake Griffin, also managed the rare feat of airballing two charity tosses in a row.

The one saving grace for Griffin is that he’s a 66.5% career free throw shooter, as opposed to Jordan’s 42.5% mark.

7. Brady Morningstar Shoots Ball to Himself

Former Kansas Jayhawks guard Brady Morningstar is the best shooter on this list, hitting 41.8% from the three-point line and 73.6% from the line.

So you’ll have to excuse him for shooting the ball to himself, then doing a running one-footer on the second attempt.

8. Andris Biedrins Is Just a Few Feet Off

Playing for Golden State from 2004-2013, Andris Biedrins just missed out on the golden age for the Warriors.

Perhaps free throws like this one are a reason why the .500 career free throw shooter decided to retire.

9. Tony Parker Shoots His Worst Shot Ever

Like Kansas’ Morningstar, Tony Parker is another example of how good shooters can have awful slip-ups. We’ll have to forgive the 4-time NBA champion and 6-time All-Star for this one.

10. Ref Courtney Kirkland Tries Blocking Kris Humprhies

This last one isn’t because Kris Humprhies had a terrible-looking free throw attempt. It’s because referee Courtney Kirkland went all-out to try and block Humphries as a substitution was being made.

Unphased by the ref’s defense, the Brooklyn Nets player would go on to hit his next attempt.