The Long and Winding Journey of Jeffree Star - YouTube's Wonder Boy

Famed YouTuber Jeffree Star is not just another beauty vlogger or social media celebrity, he's become a phenomenon. You either love him or you hate him, but no one can remain indifferent to his eccentric personality.


Star wasn't always on top of the world. He experienced his fair share of hardships, and was involved in a number of  scandals and disputes. While he gained immensely from becoming a star, he also sacrificed a lot over the years. Star is full of mysteries and there are a lot of unanswered questions surrounding his life and experiences. What happened to his music career after he was labeled "The Next Lady Gaga"? What happened between him and Paris Hilton? Why does Kylie Jenner hate him? Did he undergo any plastic surgery?

Here are Some Answers to the Most Interesting Questions about Jeffree Star >>>

A Complicated Childhood

Even though he's a star today, things haven't always been easy for the beloved vlogger.

His father’s suicide was one of his biggest heartaches and the memories haunted him throughout his childhood and adult life. Thankfully, he was left with a guardian angel, his mother.


A Mother’s Love and Guidance

After the traumatic death of his father, Jeffree learned to heavily depend on his mother who became his confidant and best friend. Laurie, his mother, was always with Jeffree; she became his number one fan and had supported him in everything he did.

As an awkward-looking and physically weak young boy, it was never easy for Jeffree to make friends his age. He always felt different from other children and knew that there was something inside him that set him apart. He felt trapped in his body, and longed to be free.


The Discovery of His Passion

Finally feeling secure in himself, Jeffree went to school everyday proudly wearing makeup. He was met with a lot of disgust and criticism from his peers. As always, his mother came to the rescue and fought with the school administration on his behalf so he could be free  to wear makeup and express his true self. Jeffree was so happy that day he hugged his mother for hours!

A Teenage Dream

Once Jeffree discovered his passion and talent for cosmetics and make-up, he was determined to pursue it.  He practiced every day; at first, experimenting with his mother’s make-up kits. His mother became his first and favorite model.

Once he mustered enough confidence, Jeffree passionately went out of his comfort zone and started to offer his services to some of his classmates and friends. Their reactions were heartwarming and inspiring. Jeffree was truly blessed with golden hands.

Moving to the Entertainment Capital of the World

Deep down, Jeffree knew he was destined for greatness His dreams were far and wide. From a distance, he imagined himself in the busy clubs of Los Angeles. He knew he needed a larger stage to express his skills and talents. The bustling city of Los Angeles was calling him.

Immediately after graduation, the young and confident makeup artist in the making flew to LA on his own. He was not a rich man and there was no lavish apartment waiting for him in the city. All he had was his belief that he was born to shake up Hollywood. Could it be true that this was his destiny?

Fighting for Survival

Living in LA was no easy feat for Jeffree. He had to take multiple jobs in order to support himself, including  various makeup jobs and modeling gigs. He worked all day and all night. However, Jeffree Star knew that aside from using his physical skills, he also needed to use his secret weapon - his wits.

Jeffree knew where to go to see the people who could help him make his way to the top. Instead of taking advantage of weekends to rest, Jeffree would dress up in attention-grabbing outfits, often mini-dresses and 9-inch-heels. He would use a fake ID to get into the hottest Hollywood clubs and try his luck with celebrities. What a dangerous game he played!

The Struggles of Making Valuable Connections

One night when he was up partying in a posh, celebrity-filled club, his eyes caught a glimpse of  the famous Kelly Osbourne. He successfully followed the celebrity inside by telling the doorman he was Kelly’s makeup artist. With that risky  lie, Jeffree and his friend were given VIP treatment.

Jeffree realized this was  a once in a lifetime opportunity and he made sure he would bag the trophy that night. He did what he does best on the dance floor and his efforts paid off. Kelly Osbourne noticed Jeffree’s outrageous yet eye-catching makeup, and the British singer and songwriter approached him. Her message would change his life forever.

The Wheels Were Set in Motion

Kelly Osbourne asked Jeffree Star to do her makeup. She even asked for his number, generously telling him that she would refer him to her friends. That night, Jeffree felt like he was on cloud nine. His dreams finally seemed to be coming true.

After his meeting with Osbourne, Star’s business began to grow and he used his distinct charm to continue to lure celebrities into contracting him for makeup work. Of course, he was not just a sweet talker, but really had the skills and talent to back up his words.

In addition to giving celebrities the kind of makeup that seemed to take them years back in time, he also gave them helpful makeup and skincare tips that really worked. Among his most notable clients were Nicole Richie and Paris Hilton. Slowly but surely, Jeffree was starting to make his mark in his chosen field. But this was only the beginning.

The Modeling World

While makeup was his first real passion, important people began to notice Jeffree’s unique charm and fashion statement. He was one of the few androgynous faces in the business, and this really made people pay attention to him. With his daring looks, intricate tattoos, and amusing wit, he was eventually offered a modeling career.

The young makeup artist sure rocked the modeling industry with his gender-bending electro look. He was much more than just makeup, pink hair, short skirts, and tattoos. This was just the beginning and he was continuously evolving.

He Dominated MySpace

Jeffree Star is an artist with an overflowing talent who needed an outlet to express himself. Fortunately, MySpace launched in 2003 and provided Jeffree with the perfect platform to showcase his thoughts and talent. On his Myspace account, Jeffree shared a variety of photos featuring his amazing works of art related to makeup, and wrote blog posts discussing his life and values.

His wild and blunt views about life grabbed the attention of both the famous and unfamous alike.In addition to his fans, Jeffree had his fair share of critics,  however, he didn’t care what others thought of him as long as he was being true to himself. In 2006, Jeffree Star became the most followed person on MySpace and more and more doors kept opening for him.

The Music Industry Called Him as Well

From being a makeup artist to a well-known model with a massive base of fans and followers, Jeffree Star was undoubtedly a success. And yet, whenever he found himself alone in his house, he would scrabble notes and write a few lines to express his underlying feelings.  His passion for music was hidden for a long time but then it was unleashed rather unexpectedly.

Jeffree would go to some of his friends’ houses and record songs out of the blue. He was into the sounds of Spice Girls, Slayer, and Lil’ Kim. He uploaded all his recordings to his Myspace account, and because of this his followers doubled.  It was time to give his music career more serious attention.

Jeffree Star Devoted Himself to Music

His serious music career started when he met Peaches’ drummer Samantha Maloney who inspired and encouraged him to pursue music. In 2009, he released his first album, which he had started recording in 2007. The album reached number 7 on the US Billboard Top Electronic Albums chart.

Jeffree began writing pop-dance songs with upbeat music, sexually charged lines, and catchy lyrics.The public loved his music and he became one of those amateur artists who always managed to gather a big crowd no matter where they are. More and more fans were becoming interested in his work and decided to follow him and his music on MySpace.

He Achieved his Own Spotlight

With his talents and growing circle of friends, Jeffree’s self-confidence increased and he learned how to better socialize and deal with both fans and critics.

Although no one could undermine his hard-won success, Jeffree kept thinking about how to learn more and further develop his skills. Despite already having a lot on his plate, the successful makeup artist turned model turned singer/songwriter decided to widen his scope even more. What did he do?

A Gold Mine in Youtube

Following Youtube’s launch in 2005, people began to shift from MySpace to Youtube, and so did Jeffree. At first, the versatile artist watched how vloggers started to dominate the platform.

Seeing how many people used Youtube to share inspiring videos and messages, Jeffree decided to become a vlogger. He shot a video featuring himself, sharing reviews and makeup tutorials to his viewers. He uploaded his first video to Youtube in February 2006.

He Started Gaining Viewers

With pure intentions and honesty, fans came to naturally love Jeffree and to support his career as a makeup artist, singer and vlogger.  From 2006 on, Jeffree uploaded a lot of content to his YouTube page, ranging from reviews about makeup products to tutorials about various makeup styles - all with  his unique style and personal charm.

Beginnings are always the hardest and Jeffree worked hard to gain popularity and bring audiences to his YouTube videos. All the hard work was worth it because he was doing what he loved and knew best. Eventually his fan-base and YouTube subscribers began to steadily increase. Jeffree loved what he was doing on YouTube and managed to do it alongside his music career.

He Had Plastic Surgeries

Despite always trying to look his best with makeup, Jeffree eventually decided to undergo several plastic surgeries. His goal was to look more feminine, but he was still unsure whether to cross the boundary of his natural gender.

For Jeffree, there was nothing to be ashamed of. He even shared documentation of his gradual changes. His surgeries did not totally change the way he looked, but he felt good about their outcome.  He underwent a facelift to tighten his skin and get rid of his wrinkles. Moreover, he went to cosmetic surgeons for several lip injections and jaw surgery. Would he ever stop?

Turning Nights Into Days

With so much going on, one has to wonder how Jeffree was able to balance it all. However, he seemed to have the energy of Superman. He successfully balanced his three thriving careers as a makeup artist and vlogger, a model and a singer/songwriter.

In 2010, Jeffree had an agreement to collaborate with Akon and join his record label. Together they planned to release a second album. Akon even labeled Star as “the next Lady Gaga.” Jeffree’s music career continued to grow and he appeared in Kesha’s music video for “Take It Off.”  He also worked with several other musical performers such as Blood on the Dance Floor, Deuce, Millionaires, and Larry Tee. However, for unknown reasons, Star left the music industry in 2013, which came as a shock to many.

There Were Plenty of Speculations

Jeffree Star’s sudden exit from the music industry left many of his fans confused. People speculated that his exit might be a result of a conflict that happened right after he signed with Akon’s record label. Jeffree had even mentioned once that working with Akon was the biggest mistake he ever made.

YouTuber and actor Shane Dawson revealed that the real reason for Jeffree’s exit from the music industry was due to bankruptcy. However, questions and secrecy still surround Jeffree’s abrupt departure. Despite leaving the music industry, Star definitely left his mark with over 25 million streams of his music. Was this the end of the road for the versatile artist?

The Great Comeback

Like the protagonist in every story, Jeffree’s downfall made him even stronger and more fearless. Deep down, he always knew what his first love was. He returned to his first love, makeup and fashion, and was determined more than ever to pursue this dream until he retired.

With his undying passion for beauty and fashion revived, Jeffree Star launched his own makeup line in 2014 named Jeffree Star Cosmetics. He even commissioned a website for his own cosmetic line where he revealed his talent and obsession, which started when he was 13. Things were once again looking up for Star.

He Leveled Up His Business

Jeffree Star Cosmetics offers a lipstick range known as Velour Liquid Lipstick, which was the first of its kind. It included a total of  31 shades of lipstick.

He also extended his line with a collection of highly pigmented highlighters called Skin Frost, which reflected his obsession with “blinding” highlighters. All of Jeffree’s products were sold out within minutes!

A Real Star

With all this success, Jeffree felt a growing need to give back to his community. He decided to widen his social media platforms so he could give more to his fans. He was extremely happy to see that his affect on his audience remained the same.  In a span of a few years, Jeffree Star gained almost 9 million followers on Instagram, 2.6 million likes on his Facebook page, 2.8 million followers on Twitter, and over a million followers on Snapchat. These numbers are mind-boggling, yet despite his super-stardom, he still felt incomplete.

It was Time for Community Payback

Even with all his success, Jeffree  knew deep inside that he could still do more. He saw that he could inspire a massive amount of his social media followers and he wanted to double his efforts  to ensure the unwavering support of his fans.

The makeup artist promised to himself that he would never get tired of creating makeup tutorials and videos that people of all ages and from all walks of life can watch and learn from. His goal was to inspire his fans, and he knew that in his own way, he was making a difference in people’s lives.

An Amazing Makeup Teacher and Guru

Jeffrey knew that in order to be an effective source of inspiration, he must be brutally honest. He never made  fake reviews about products, even if large companies came to his doorstep.

Star only delivers honest endorsements. Keeping in line with this value, he ensured his fans that his own makeup line would never release a product that did  not pass his ultra-high standards. First and foremost, Jeffree is concerned with the safety of the user and wants everyone to get a fair share of information about cosmetics. He gradually  became a makeup teacher and guru, and even the most famous celebrities came to love him.

He Had His Own Series of Controversies

Star’s success didn’t happen overnight, yet the hardships he went through only made him stronger and able to better appreciate how far he had come Like any other famous individual, he also encountered several controversies, including racism.

He had a conflict with Kat Von D after withdrawing his ties from her. He also had an issue with Kylie Jenner after posting a negative review of Kylie’s lip kits and the foundation’s packaging.

His Tactfulness and Honesty Made a Lovable Combination

Jeffree experienced a lot of controversies, yet only those that involved famous celebrities shook the Internet. After receiving a mix of positive and negative comments, Jeffree knew he had to maintain the balance, and so he did what he felt was right.


He posted a video on his channel where he explained the issues to his audience and offered an apology. In the video, Jeffree told his viewers how he regretted saying those disgusting and nasty words and that he is willing to change. Being true to himself and truly apologetic, he received forgiveness and massive support from fans.  

A Proud LGBT Member

Jeffree’s fearless and straightforward attitude made him a leading force in the LGBT movement. His stand on gender equality encouraged the LGBT community to be true to themselves. He also addressed critics and haters through his blog.

Jeffree is never ashamed to show that beneath all his heavy, perfect makeup, there’s still a genuine and lovable guy. He is gay and he’s very proud of his gender. Love from his fans and supporters kept him alive and kicking, as did his philosophy and belief in life.

He is Still Far from the Finish Line

Now in his early 30's, Jeffrey knows that his success would never have been possible without his mother and all the people who believed in him. This success can also be attributed to the people who doubted his skills and capabilities.  However, he knows his journey is still far from over.

Rumor has it that Jeffree Star plans to launch another line of cosmetics. He is open and honest about his goals and fans can continue to expect new videos from him. There is no doubt that Star will continue teaching, inspiring and helping his fans achieve the best version of themselves.