It’s rare for a mega-celebrity sibling to bust out of the shadow of the popular one. Janet Jackson and Ashley Judd are exceptions. I’m sure there are others, but you ever notice that there is a certain pattern that the siblings go down:
Pregnancy & Marriage= Ashlee Simpson & Solange Knowles took this route. Ashlee, who in my opinion makes better music than her big sis Jessica had quite a year. The current red hair got married and had a baby! I’m too happy for her. I thought for sure Nick & Jessica would have the baby first, but once Jessica’s marriage fell apart so did her career. Solange had huge shoes to follow. I think she just said F-it, I’m the rebellious one. I’m F-ing, I’m smoking and I can bet your bottom dollar she gave poppa mad lip on being forced to marry. Let’s not forget Jamie Lynn Spears…yeah she got pregnant at a very young age, yes she should’ve known better at least she’s not marrying just because…
Whore It= Ray J. Remember how he eased his way on Moesha twice playing two different characters? Nepotism at it’s best. Every interview he was in they always asked about Brandy. Everyone referred to Ray J as Brady’s little brother. Fast forward a couple of years I’m just amazed how Brandy is asked about her younger brother in interviews. Ever since Ray J made a sex tape with his then girlfriend Kim Kardasian Ray J’s career and lust life has jolted. Sexy Can I is still my jam. LaToya Jackson whored it up too for Playboy. Ali Lohan…crickets right? Lindsay’s younger sister who attempted to have a hit reality television show.
Drugs & Alcohol= The only person I could think of was Stephen Baldwin on this one.
Stay Out The Spotlight= I love the sibling that stays out of the spotlight, but still manages to be fly. I would say that Nikki Hilton does this the best.

Nikki Hilton in her closet.
Am I missing any other catergory for celebrity siblings? Did I fail to mention someone?