Jimmy Evans (James Remar)
Grey's latest casualty, Alex Karev's father Jimmy Evans, died a relatively peaceful death on the winter premiere episode after a pretty tumultuous recurring role throughout Season 10. A former heroin addict and current alcoholic who beat his wife and sons when they were younger, Evans ditched Karev and his siblings early in life. As such, Karev has daddy issues, which manifested in a major way earlier this season after his girlfriend Jo proved Karev's patient was actually his father. Evans' health goes downhill after complications from his alcohol and drug abuse lead to cardiac arrest and, subsequently, a botched surgery at the hands of sleep-deprived, ego-trippin' intern Shane. Karev forgives his dad, tells him it's OK to let go, and says goodbye for the last time.
Heather Brooks (Tina Majorino)
She may have been a bit over-eager, but we liked Brooks. She was shaping up to be a real contender for favorite resident. One of five new surgical interns who came to Seattle Grace (now known as Grey Sloan Memorial Hospital) during Season 9, Brooks starts her internship off with a bang… um, literally — she and Karev enjoy a few good romps in the on-call room. She is handpicked by Derek Shepherd to be "his" intern and train in the neurosurgical field, and she becomes a favorite of Dr. McDreamy and his wife, Meredith Grey. Brooks tragically dies in the Season 10 premiere, after she gets electrocuted in the basement trying to find Dr. Webber. Shepherd attempts surgery to save her life, but to no avail.
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Adele Webber (Loretta Devine)
Chief Richard Webber's wife, Adele Webber, suffers through the last few seasons of her time on Grey's Anatomy with Alzheimer's. Even though Meredith Grey tampers with her and Shepherd's Alzheimer's drug trial to get Adele the medicine she needs, Adele's Alzheimer's continues to get worse. On the way to Bailey's wedding, Richard receives a call from the hospital telling him that Adele is on the way to the hospital. Bailey and Richard head to the hospital together, where Bailey immediately begins to work on Adele. They ended up working on her together, though, nearly causing Bailey to totally miss her own wedding. While the talented surgeons were able to save Adele's life on the table, the surgery proved too stressful for her heart and she died of a heart attack soon after.
Mark Sloan (Eric Dane)
Remember when Mark Sloan first came to Seattle Grace? Hello, Dr. McSteamy! Sure, he was a bit of a philanderer who wrecked Addison and Derek's marriage in the beginning of the series, but his growth and benevolence later more than made up for his initial shortcomings. He really made us swoon over his love for on/off girlfriend Lexie Grey, which ultimately kind of ended up being the death of him. When he, Lexie and several other Seattle Grace doctors go down in a plane crash, Lexie gets crushed beneath debris from the plane and dies. Sloan confesses his undying devotion to her in her final moments, lamenting that they were "supposed to end up together. We're meant to be." Although it appears for a time that he'll overcome his injuries, you get the sense the fight is gone from him now that he's lost Lexie, and he ultimately slips into a coma and dies in the Season 9 premiere.
Lexie Gray (Chyler Leigh)
Kind of just gave this one away, huh? To be honest, we're still not really over this one. Lexie was smart, she was funny and she had a lot more going on upstairs than the Grey's average medical intern. Known particularly for her photographic memory, "Lexipedia" had grown on everyone over the years, including her half-sister Meredith. But, alas, during the Season 8 finale, as she and other doctors struggle to stay alive injured in the wilderness after their plane crash, Lexie dies — in quite possibly the most crushing (literally and figuratively) Grey's Anatomy death scene ev-er.
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Henry Burton (Scott Foley)
Oh, Scott Foley, how we love thee. We were super-excited when Foley came to Grey's Anatomy as Henry Burton, a lifelong diabetic who makes Dr. Teddy Altman believe in love again. True, she married him at first so that he could benefit from her insurance and get the surgery he needed. But ultimately, their marriage of convenience turned into a real marriage when, in the Season 8 finale, she chooses Henry over going to Germany with her on/off boyfriend Dr. Perkins. They kissed, we swooned, and then he died. OK, the sequence of events was a bit more spaced out than that, but when he died during surgery performed by Dr. Yang, let's just say we died a little too.
Denny Duquette (Jeffrey Dean Morgan)
A heart patient at the hospital, Denny Duquette becomes friends with Izzie Stevens early in his stay. While he is waiting for a heart transplant, he and Stevens actually fall in love and get engaged. In a desperate move, Stevens cuts Duquette's LAVD wire, getting him a new heart. Unfortunately, he develops a blood clot and dies. Le sigh... another one bites the dust. Our grief was momentarily tempered in Seasons 3 and 5 when Stevens starts seeing him everywhere but, sadly, it turns out he is actually just a symptom of her brain tumor.
George O'Malley (T.R. Knight)
The first real heartbreaker on Grey's was the tragic death of everyone's buddy, George O'Malley. He'd finally come out on the other side of his drama with fellow resident Izzie Stevens and his wife-for-a-hot-minute Callie Torres, and was totally hitting his stride. When he decided to follow in the military footsteps of Dr. Hunt and enlist in the Army, we knew he was probably leaving the show. However, we didn't realize his exit would be quite so dramatic — on his way to tell his mom about enlisting, he jumps in front of a bus to save a woman's life, sacrificing himself instead. He later dies in surgery, after a brief period of being the bandaged man whose identity is unknown .