The craziest celebrities are the ones that stay at the tip of our minds even after we see their last breath of day. Now that times have changed and we notice a different side of the music business, the harsh reality is musicians must consistently be seen doing unthinkable acts by the paparazzi to be relevant in the game. Even introverts like The Weeknd need to show their faces every once in a while, or they will quickly be forgotten in favor of an artist that can party hard.

The lifestyle of red carpet events, drugs, groupies and scandals can only last for so long. A few of the most infamous party animals such as Anthony Kiedis from the Red Hot Chilli Peppers had to put it to rest. The other side of a musician's lifestyle is most of the time represented by rappers, rock artists, and R&B singers dishing out lyrics about being in the VIP at a club or waking up the next morning not remembering what happened the night before. Most fans are expecting them to live up to the expectation and if not, they are considered boring. Who wants to pay $100 concert ticket to watch a dull artist?

What we see on TV rarely matches the reality of these entertainers' finances. Yes, we see the fancy mansions, decked out cars, a Rolex on the right arm or diamond grills in their teeth but it is only a small percentage of the truth. Let’s say it together everyone; music – business. Eighty percent is business, and twenty percent is what we enjoy as entertainment. It means the money can come quick like a train but might also disappear as fast as a one-hit wonder.

15. Rihanna - Was $9 Million In Debt

Rihanna is the epitome of pop star success. She is exotic, talented, funny, two-dimensional and has a net worth of $160 million. While the "Work, Work, Work" artist has wooed the hearts of fans worldwide, Rihanna has also run into cash flow problems in 2009. It does not come as a surprise because this was around the time she was in an abusive relationship with her then-boyfriend Chris Brown. Despite this fact, Miss Robyn Fenty pointed fingers at her accountant, alleging that he gave her terrible financial advice leading to her being $9 million in the hole. How can this happen, you ask? Let’s see. When Rihanna was dating, Chris Brown the both were in and out of night clubs as they fell in love, popped bottles and promoted themselves as artists.

As a native Bajan (Barbadian), Rihanna is a jet setter that quite often visits her hometown. We also need to add that her best friend Melissa Forde has been a part of her entourage, traveling with Rihanna almost everywhere she goes. I doubt she is helping RiRi pay for first class flights and trips around the world while she is on tour. Nonetheless, most of her money went to purchasing a $7 million property that her accountant told her was okay to buy despite her over the top expenses. We’re rooting for you RiRi! We know you can keep pumping out hits to make up for your loss.

A lesson to learn here is no matter how your romantic relationship can get, put the same effort into making sure that you don't overspend.

14. Ozzy Osbourne - Owed $1.7 Million In Taxes, Bought a Chicken Coop

Ozzy Osbourne was at the height of his career in the 1980s when his album Blizzard of Oz went multi-platinum. He was energetic, fun, crazy; a natural born leader before and after he left his group The Black Sabbath. If you felt entertained while watching his MTV-reality show The Osbourne’s in the early 2000s, you could tell that the rock star persona was still in him despite having two children and a wife. Despite the family oriented/dysfunctional vibes on the show, there is one thing that Ozzy couldn’t resist while in his 20s, and that was quote on quote, partying like a rock star. He even has a single on the Buffy the Vampire Slayer soundtrack named “Party with the Animals.” What exactly does that mean? I’ll fill you in on the examples:

His previous wife named Thelma Riley started to have enough of his partying. She went as far as buying a chicken coop, leaving him responsible for feeding his chickens at night. To show his wife he was unable to be tamed, he lit the coop on fire while shooting a gun. I can only imagine what she was going through.

Thankfully enough, later on in life when Ozzy had financial troubles he and his current wife Sharon Osbourne pulled through and paid $1.7 million in back taxes. Now, that’s what I call a success story!

13. Andrew W.K. - Blew All His Money Partying, But Smartened Up

Andrew Fetterly Wilkes-Krier (aka Andrew W.K.) is a musician, music producer and songwriter who made popular hits such as “We Want Fun” and “Party Hard.” Not to say that Ozzy Osbourne had anything to do with his financial shortfall but Andrew was a headliner for Ozzy’s annual music festival called Ozzfest in 2001. A few of Andrew’s hit songs including “It’s Time to Party” were used in video games in addition to commercials. Wow! He must have been racking in a lot of money. Andrew W.K. considers himself to be a professional partier with no grasp of managing his finances.

He has admitted to spending most of his money on partying because of hearing negative phrases from friends such as “money is the root of all evil” as he was growing up. Later, in life, a wise person in his circle told him that money could be good and bad. It depends on how people use it. As Andrew reminisced on the past, he thought about how he could have achieved more goals if he had handled it correctly. This guy might seem like an airhead because of the titles of his hit songs, but he came to realize that if you are poor, there is no way you can help other people and began spending his money more wisely on his family.

What is the moral of Andrew’s story? Be weary of people that have bad money habits and beliefs that will make you think that money is negative.

12. Puff Daddy (aka Sean Puffy Combs) - Has Had Artists Claim He Stole Their Money

It seems that Puff Daddy has the world at his fingertips. Starting as an intern with Uptown Records after dropping out of Howard University turned out quite well for him. He is infamous in Miami for throwing all-white parties, and if you search his name with the word party, Google Image pages will tell the rest. Although the late Notorious B.I.G. is no longer with us, Puff Daddy helped birth the careers of many artists including French Montana, Mase, Bow Wow and the list goes on. Besides music, he made a smart decision to diversify his portfolio and opened a restaurant in 1998 located in the hot city of Atlanta called Justin’s, which is the name of one of his sons.

In 2009 the IRS searched high and wide for Puff Daddy for a slightly over $7,000 back tax check for the restaurant. As a business man that always appears to be well dressed and so eloquent with his words, how can anyone miss that? Well, we all know that Puffy is known for partying and after popping bottles in the club for too many nights, forgetting to pay taxes for a business that is in another state can happen to anyone.

Aside from his restaurant, there have been many of his artists that have come out of the woodwork admitting that Puffy cheated them out of money from music albums. The artists include the rap group The Lox, R&B singer Carl Thomas, and "Whoa!" Hit rapper Black Rob. No matter what Puffy is going through, the right thing to do is pay his artists for their hard work.

10. Lindsay Lohan - Couldn't Stay Away from the IRS or Jail

She’s back! Yes, Lindsay Lohan is back in tinsel town. Not on the Hollywood scene but she pops up occasionally, in the news stories. Most know her for being an actress, but she is also a singer with four albums. I remember her as the innocent Disney star with bright red hair. I thought she was going to maintain the girl next door image. In the mid-2000s right before her career started to take a downturn, Lindsay would show up to movie sets late, became friends with Paris Hilson was pictured with Snoop Dog in the club and was proud of her behavior so much that she had a cameo in Pharrell Williams music video Everybody Knows. An infamous song about crazy things that happen at night clubs. Like Puff Daddy, the IRS came looking for her when she owed $250,000 in 2012 after she went bankrupt. After finding out that she had no plans to pay up, the IRS stopped her assets. Surprisingly enough, her celebrity friend Charlie Sheen helped her out with $100,000.

Four years later it seems that her partying ways remain. We can at least say that she was close to being domesticated; she was recently engaged to a Russian Billionaire heir named Egor Tarabasov, later breaking up with him for his violent behavior. Well, it is never too late to get back on your feet Lindsay.

One of the points we can learn from her story is there is nothing wrong with being a good girl. They usually last longer in their career and make better financial decisions.

10. George Clinton - Lost All His Money To Financial Advisers 

What is the first thing you think about when you hear the name, George Clinton? If you ask me, I reflect on the multi-colored dreadlocks and the party lifestyle that baby boomers would tell me about when they reminisce on their musical favorites. He had a good time performing with his bands Parliament and Funkadelic and earned the respect of the great James Brown. As he was traveling the globe with his band, taking part in some of the best parties while brushing shoulders with celebrities, he failed to pay attention to the little details of his compensation from the record label that he deserved. George went on the record to say that he earned less money than his fans thought.

He had no idea that his business partners and managers took ownership of the publishing rights to all his music. If he played his cards right, he could have retired earlier on in life. Owning the publishing rights to hit music means receiving a check every month in the mail. In 1984 Mr. Clinton, unfortunately, filed for bankruptcy to avoid an economic mess. On a more positive note, George Clinton’s last day on tour in 2016 is on December 31 in Las Vegas. He also has a book that was published in 2014 out right now called “Brothas Be, Yo Like George, Ain’t That Funkin’ Kinda Hard on You? A Memoir.” Who knows? With all the tours, he had lined up this year and his book; there’s a possibility that he can get himself back in the green.

9. Allen Iverson - Thankfully Will Get $30 Million When He Turns 55

Allen Iverson wore many hats as an NBA player including being a rapper. It is common as a matter of fact for most athletes to want to step into the studio. I once asked one of my NBA obsessed friends what happened to Allen Iverson? Nothing had me more prepared than watching a documentary on Netflix of him called Iverson. He had a whirlwind of media scandal’s, and it doesn’t help that his cornrows (at a time when they weren’t a favorite of the NBA), and his thug-life persona was intimidating to society, although he was known as being one of the top shooting guards ever to live.

Allen Iverson lived a lifestyle behind the scene like most American athletes. He partied a lot, and the money gave him a bit more pep in his step to the point when he thought he could say controversial comments to the press and get away with it. Sources state that he made up to $200 million throughout his career, mostly from his endorsement deals. In addition to fancy jewelry, real estate, and fast cars it started to override his fame and when the day came that the courts garnished his bank account, it was a life awakening event. He opened his statement and noticed a $900,000 deficit for payment towards jewelry. Out of all the organizations that he can thank for an opportunity is Reebok. He apparently has a $30 million trust with the shoe company that will become available the minute he turns 55 years old.

8. Amy Winehouse - Did Not Have a Will

Amy Winehouse had a heart full of soul, broke boundaries of what jazzy rhythm and blues looked like, lived her life like a rock star and her meltdown was captured by media for the world to see. Even until today, new artists from the UK mimic her singing style to continue the legacy of Miss Winehouse. Before she died, Amy was married to Blake Fielder, who many blame her excessive partying and drug addiction due to the emotional abuse that he imposed on the creative songstress. Shortly after they got married, we started to see a different Amy Winehouse. After a crazy night of partying, the paparazzi caught her walking barefoot around London town. She was drastically losing weight because of her drug addictions. Her voice was taking a toll and news outlets publicized that her performances including the one in Dubai in February 2011 were a disappointment.

Her estate was said to be worth over £4 million which equals $6.7 million in US dollars. However, with her additional debts and taxes that needed payment, the most disappointing part of this story is she did not write up a will before she left to give what was left over to family and loves ones. At the end of the day from a financial perspective Amy Winehouse lost out big time; when our time to go comes we can’t take the money with us which means the tax man and other non-family sources took over what she worked so hard for.

7. Luke Campbell - Thought He Was Too Cool For The IRS

If you don’t know about Luther Campbell, get ready to learn today. Luther is infamous for making hit music (that in my opinion) started the campaign of booty shaking songs all over the world in the early 1990s. If you think misogynistic music is bad now, imagine how much it was not accepted back, then. The lyrics in his music stirred controversy and here’s how it happened. In 1989 he was in a group called As Nasty As They Wanna Be and a hit single on the album caught the attention of the American Family Association (AF) leading to court visits for making obscene music.

Now to get back to the topic, Luther Campbell was the Jamie Foxx of our time throwing over the top parties with women in itty-bitty swimsuits with rappers, R&B singers, rock stars and their entourages all in one house. Although he is known for starting a musical trend that brought him millions of dollars, he had to pay off legal fees for his raunchy lyrics and was also unable to pay the IRS $74,000 in taxes in 2012. To go back in history, his record label Luke Records went into bankruptcy. At the end of the day, Luther now works a few jobs as a Miami New Times writer and is the coach for a Pee Wee football team.

What can we learn from Luke’s story? Watch your words, actions and what you write. It might offend someone and if you decide to cross the line, make sure it is timely. Breaking the mold in a traditional industry might sound genius but give it time and break down barriers when the time is right.

6. Lil Wayne - Spends $55,000 a Month on a Jet

Lately, Lil Wayne has been in the tabloids more for his lifestyle versus his legacy of making epic music. He is one of the few mainstream rappers that was good enough to sit in on an interview with Katie Couric in 2009 on her talk show named Katie. Wealthy Millennials in the suburbs flocked to his skateboard riding persona even though his lyrics about being ghetto fabulous were not even close to their reality.

The one thing that Lil Wayne or his public relations team can’t deny is the man partied more than a DJ. He has even spent $30,000 at Diamonds club in less than 3 hours. A $30,000 donation to an organization for in-need families would have been a better expenditure! Nonetheless, the stories about his career with Cash Money Records were leaked, his $55,000 a month jet and $30 million worth of fine art in his Miami Beach castle were re-possessed. I need to add that he also owes $2 million to a company named Signature Group, and is still in financial dispute with Cash Money Records owner Birdman for money from previous albums he hasn’t received. My goodness. I hope that Lil Wayne figures it out or gives us another great album to take care of his situation.

The lesson today from Lil Wayne’s lifestyle is to curb expensive addictions and pay attention to the small details of money you spend. Partying is a luxury, but when the year ends, and you have nothing to show for, the only person you can hold accountable is yourself.

5. James Hetfield - Wasted Money on Drugs and Alcohol Forcing Them To Keep Working

If you have a debate with your friends about the best rock band ever to exist, Metallica might end up in the conversation. This group has traveled to perform in all the great cities worldwide. North America loves a lifestyle train wreck to success story no matter who it is, and it helps even more if you are a musician. James Hetfield admitted to cleaning up his act after a long time of drinking excessive alcohol and being addicted to extracurricular drugs. In 2001 he became sober and got his life back on track. Woo hoo!

Even an alcoholic with a resilient liver can’t fight off the way it impairs your mind, lessens the number of brain cells to improve memory and makes you make irrational decisions. James and the group hired staff they could not afford and were unable to keep up with an entertainment corporation. Because of the mishaps, Metallica cannot retire; they have to tour every summer to make up for the loss. They tried to create a movie, but unfortunately, the film Through the Never flopped. It was over budget, and if successful, it could have helped them out with a chunk of their debt. As one of the thought to be richest bands in the world, James has a lot of work ahead of him.

To all of the upcoming rockers reading this story. Do your best not to let this happen to you.

4. The Goo Goo Dolls - Made $0 Off Album 

Another fete passionate group, the Goo Goo Dolls, made our list. While we wish they had a better story ending with the success of their musical catalog, it looks like fun parties and keeping up with the Joneses was one part of the business this band couldn’t resist. More recently in 2013, Johnny Rzeznik, the lead man in the group stopped drinking. He told CNN "I quit drinking. And that lightened up my perspective on the world quite a bit... I think our last album was a bummer. But the only way out is to go through, so that was going through. And now we're out on the other end."

In the 1990s the band sold over 2 million albums while under contract with Warner Bros. Even after the Goo Goo Dolls owed Warner Bros. money, the record label was kind enough to give them an advance after completing the Dizzy Up the Girl album in 1998. Until this day, none of the members have seen one penny of royalties from earnings for the album. It makes full sense that the strategy for the record label to request an album was to recoup the money. We would think that the three members learned from their partying ways back in the day, but more recently they surround their performances around parties.

The moral of Goo Goo Doll’s story: a rock star lifestyle can be a reality without doing things to destroy your life. In your twenties and thirties you can catch up, but if you're forty years old in the business with no assets to your name, you may have to start all over again.

3. Courtney Love - Walked Away From Nirvana Collection

When I think of Courtney Love, my mind turns to Kurt Cobain, plastic surgery and her love for the nightlife. Her first music video I can remember on MTV made me believe that she had what it took to be the next Madonna or being respected much like her counterpart (back then) Gwen Stefani. Whether it was her personal issues or the death of her late husband Kurt Cobain, she was the talk of the town and not for the right reasons. If you are thinking that she was caught a few times in her past for being tipsy, it is 2016 now, and she ended up booted out of a Guns N’ Roses party at Coachella for drinking too much. Who gets tossed out of a rock stars party? That means she was acting out more than a male pop artist that will get a pat on the back for his behavior. It is a belief that she is worth $150 million but let’s not get ahead of ourselves. She made $27 million of Nirvana's estate disappear; apparently, she inherited this money in 2006 after her husband died. When interviewed by the Business Insider about this she said that she “had to let it go.” If she was sober when she made this decision, her daughter Frances Bean owns the Nirvana music catalog, and after turning 40 years of age, she will be the board member of the Empire.

Note to self, never make a child responsible for an estate. While this sounds like a good way to create generational wealth, you have no idea how your son or daughter will turn out. Five percent of the Estate looks good. Twenty-five percent of the estate, even better, but be ready to groom them for the responsibility before the time comes.

2. Busta Rhymes - Forgot To Pay His Taxes

Busta Rhymes had the swag to become the next Snoop Dog. His dreadlocks, tough guy stare, heavy build and Jamaican accent in some of his songs were loved by many. If we count down the top 20 rappers of all time, he will end up on the list. We don’t know if it was his fast rapping style or his fearless New York mindset, he couldn’t shake off the nightlife. Busta Rhymes music played at night clubs, weddings, and birthday parties. It didn’t take rocket science to realize at the beginning of his career that he will carry out his lively personality we see in his music videos in night clubs in New York, and major cities he would perform in.

Much like the other artists in my article, Busta forgot to pay his taxes on time owing more than $800,000. He even dedicated partying in a rap song featuring Zhane named “It’s a Party” in 1996. In 2015 at an after party for the BET awards, Busta ended up being in a club where a shooting took place. He was with rappers Meek Mill, The Game, and T-Pain.

Also, he is the life of the party so much that fashion designer Alexander Wang called him on stage at his after-party in September 2012. When a successful fashion designer invites you to a party, you know you made it in life. Busta is also a good time Charlie with prim and proper celebrities. In 1997 the cookie cutter Martha Stewart took pictures with him on the red carpet at the MTV Music Awards.

1. Tupac Against the World - Was Worth $40 Million But Died With Under $100,000

When you are an artist signed to a music label named Death Row Records it is probably a part of your contract to live out the life of a real gangster. Tupac Shakur was a man of many faces; besides the one we know the most, he was an activist, critic of politics, and an avid reader of the sciences. That is not bad for a gangster rapper! At the same time, Tupac had his share of run-ins with the law and had no choice but to live up to the thug life image with a boss like Suge Knight. He was conflicted between being a simple man or pursuing a new career. Before the end of his demise, Tupac Shakur wanted to turn his skills that he learned as an actor in Gridlock’d (co-starring the British actor Tim Roth) into working in front of the big screen. There are many theories out there as to why he is dead; Tupac wanted out of Death Row Records to change careers or the hip hop beef with the Notorious B.I.G.

At the end of the day, the most shocking part of his lifestyle is he died with only $60,000 in the bank. Say what? How can a man with a net worth of $40 million die with less than a $100,000 to his name? Here’s the answer. As much as he was an intellectual, Tupac loved late nights at the nightclubs. Before he passed, he was engaged to music producer Quincy Jones daughter Kidada Jones, but before then he enjoyed the presence of female groupies. His assets such as his beautiful rental house in the Kardashians hometown of Calabasas was taken care of by Suge Knight and his fancy Rolls-Royce, Mercedes-Benz and BMW on rims were all owned by Mr. Knight as well.