Chelsea Handler, Katie Show

It's a rare sight to see Chelsea Handler so vulnerable, but the funny lady did just that Friday on the Katie show.

The E! star—who is famous for her sharp tongue and witty ways—gave fans a taste of her softer side while appearing on Katie Couric's talk show where she discussed both the devastating death of her brother (he passed away in a hiking accident when Chelsea was 10) as well as her mother's lost battle to breast cancer.

"You just don't ever recover from that," Chelsea tells Couric of her brother's death with tears in her eyes. "It's not like seeing someone die, which we did experience with my mother, so for the people that are watching that, it's much easier on the people, I think, to watch somebody go because you're so mentally prepared because the other option is one day your life is OK and then the next day it's not."

Not only are the sad memories still tough for Chelsea to talk about, but she admits that her parents had an especially difficult time coping with her brother's death:  

"To see your father wake up crying and cry in front of people all the time about his first son being dead, to see that you're like…'Stop it you're supposed to protect us' so I think in my way I just got this really tough exterior," she explains. "Because I'm like 'OK I gotta get my act together because these two people are kinda falling apart.'"

Chelsea's tough exterior has undoubtedly served her well in all aspects of her life, and her strength was again put to the test when she lost her mother to breast cancer in 2006. Although it was a different type of loss than that of her brother, the Chelsea Lately star remembers her father being in denial and ultimately helping him face reality:

Watch Rick Ross on Chelsea Lately!

"Well he [my father] came in you know with like McDonalds and an Egg McMuffin. My mom's on morphine and a feeding tube and she's completely out of it and my dad walks in with the New York Times and an Egg McMuffin and he's like, 'Rita [to my mother], do you want an Egg McMuffin?' and I'm like, 'She's not going to have an Egg McMuffin, she's about to die. You need to get real with the program.'"

She continues, her eyes welling up with tears, "My mom said to me 'You need to tell your father I'm dying and you also need to get prepared because he's a nightmare,'" she said. "And when I die you're going to find out what he really is like," she adds with a chuckle as she cries.

Still, leave it to Chelsea to find the silver lining in life:

"It's a terrible thing," she said of her brother's death. "But it's an amazing thing to go through and experience because it gives you an appreciation for everyone you care about in your life."

Hey, she may be one of the biggest pranksters in the biz, but no doubt, this funny gal also has one of the biggest hearts.

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