Bobby Brown's son Bobby Brown Jr was found dead aged 28 on Wednesday at his home in Los Angeles.
The media personality, son of R&B singer Bobby Brown, died just five years after the death of his sister Bobbi Kristina, aged just 22.
Bobby appeared on his family TV show Being Bobby Brown in 2005 alongside his dad, sister Bobbi Kristina and step-mother, Whitney Houston.
His death is the latest tragedy to befall Bobby Brown, as he's lost several people close to him over the years.
Sister's boyfriend shot dead
Bobby sister’s fiancé Steven Sealy was killed aged 31 in 1995 during a shoot out, in Boston, US.
Sealy, 31, was shot in the head while sitting in Brown’s cream-colored Bentley, but the singer, who was aged 26 at the time, escaped injury, AP reported.
Brown, 26, was standing outside the car with a bodyguard at the time of the shooting.
His shooting led to a brief gun battle where dozens of shots were fired, witnesses claimed.
Sealy was shot at least three times in the face and chest, according to paramedics.
Whitney Houston's death
Bobby's ex wife Whitney Houston, regarded as one of the world's best ever divas, tragically died aged 48 in 2012.
A cocktail of nine drugs were discovered in her body when she was found face-down in the bathtub at the Beverly Hilton on February 11, 2012.
Bobby and Whitney had a rocky relationship which was filled with domestic violence and drug taking, with their personal issues often being discussed publicly.
Whitney Houston's hubby Bobby Brown says he 'scooped poo' out of wife's bum
The pair separated in 2006 and their divorce was finalised on April 24, 2007.
Whitney got custody of their their then 14-year-old daughter, Bobbi Kristina.
Following the death of Houston on February 11, 2012, six days after his 43rd birthday, he struggled to perform at a New Edition show, shouting "I love you, Whitney" as he broke down in tears.
Both Bobby's parents die
Dark family secret, drug abuse and lesbian romps – Whitney Houston's life explored
In 2011 Bobby Brown 's dad Herbert passed away after a long battle against cancer.
His death came just a month before Whitney died and within a year of Bobby's mum Carole passing away.
Carole passed away in Los Angeles. She was 69 years old.
At the time Bobby said in a statement: "It is a sad time for me right now. I am experiencing a tremendous loss, but I vow to celebrate her life in every way that I can with my entire family, including my fiancé Alicia, and my children Bobbi Kristina, Laprincia, Bobby Jr and Cassius."
Death of Bobbi Kristina
Bobby and Whitney's only child Bobbi Kristina died in 2005 just three years after her mum.
Bobbi had spent six months in a coma after suffering serious brain damage after being found unconscious in a bathtub.
Speaking in his first interview on American talk show, The Real, he said: "We prayed and hoped for six months… for something better to happen.
"But when God calls you, he calls you.”
Bobby added that he thought her mother, the late Whitney Houston, 48, would have had something to do with her death, after being found unconcious by partner Nick Gordon in the bath at home in Atlanta in January.
He said: "I'm pretty sure her mother was… had a part with like, 'Come on, let's get her up here.'"
In a civil case in 2016 Bobbi Kristina's ex boyfriend Nick Gordon was found legally responsible for her death and was ordered to pay her family $36million.
What Bobby's remaining kids are doing
Whitney Houston's disturbing autopsy report – from sewn-on wig to horrifying real teeth
Although two of Bobby's children have now died, he still has five other children.
La'Princia Brown, 30, is Bobby's daughter with Kim Brown who he dated in the late 80s
She runs a blog called Saving Princie as well as making jewelry and selling it on Etsy and is engaged to he her long-term partner Eddie Ray.
Boby's oldest child is Landon Brown, 84, was born on June 22, 1986 in Los Angeles, to Melika Williams.
Landon is an actor and assistant director, who has worked on The Nightmare Pill (2018), Post Script (2011) and Rock the Cradle (2008).
Boby has three other young kids with his current wife Alicia Etheredge.
They have a son Cassius, born last year, and daughters Bodhi Jameson Rein Brown, 5, and Hendrix Estelle Sheba Brown, 4.
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