Charlie Sheen got me thinking, when he let everyone know that "duh, every day i am winning!" Usually people that have to say that are losing, they just don't know it yet. Charlie has the one problem that always turns you into a loser: CRACK. Usually you end up in the morgue or first you lose all your money then you end up in the morgue. It can be a slow process, especially if you are rich, but unless you can admit you are currently losing (and get real help) the outcome is inevitable. Charlie, in the end, may end up being one of the biggest losers of all time.
Lebron recently said "my haters still have the same problems and i have a great life." He has to be very insecure just like Charlie to say that. "The Decision" was a real loser act, there is no disagreement there. Lebron is very money motivated and wants to be the first billionaire athlete, without at least 3 rings it won't happen. Couple the Decision with no rings and Lebron is not a top winner either!
These two jokers motivated me to post the most successful athletes and entertainers, obviously it is highly subjective. I would consider the Chief to be one of the most successful because he turned $2,500, passion and perseverance into the one of (or the most if you only go by SB rings) the most successful football franchises. But this is a list of athletes and entertainers, not business owners.
Oprah is definitely the most successful
woman entertainer, not only is she beloved but her net worth is approaching $3 billion, unbelievable! but since i am male, my post will focus on the male athletes and entertainers who are truly winning.
Ok, this kills me but Tom Brady has to be on top or near the top. He has this princess, giselle who is the most successful model in the world. she is a rock star in brazil and has established joint ventures to market lines of sandals (sold 25mm pair last year), makeup and intimates. it's no wonder that she and tom were recently seen at Carnaval, it just increases her popularity and sales of her sandals and panties (although i think a lot of women in brazil wear only thongs or nothing at all:)). the economy in brazil is booming, currently she is making between $50-100mm/yr and already has a roughly $250-350 net worth. she is very likely to become a billionaire because of her ownership in these ventures vs. licensing that most celebrities do. so tom is a kept man, with a net worth of maybe $50-100mm it is no wonder they put him on the NFL lawsuit. he has no need for $, even in a divorce he will probably be better off than he is now. that is crazy! say what you want but tom is definitely not playing for the money, in fact he is probably the best off current NFL player.
i guess he's not a bad looking guy either at least in this pic. He and giselle are building a new $20mm 22,000 sq. ft.castle and he backs it up with three SB rings. His only downside is he really can't dance (dances like a white man as they say), plus i think he may have taken the metrosexual thing a little too far. But even us haters have to recognize he is definitely winning.
but think about other super famous entertainers and athletes. all the ones i list are worth in the $500mm (except billy joel who got ripped off so he is only worth $160mm (only?) and paul mccartney is a real billionaire) range so money should never be a problem. but many of them have real kinks in their armour.
magic johson - very successful businessman and 5 NBA rings but has the AIDS. if he has any sense he should never divorce cookie b/c the dating pool is tiny (even for rich superstars) if you have the AIDS. i take that back, there is a big dating pool amongs crack and meth addicts, not necessarily a good pool just a big pool:)
tiger woods - 14 majors but went thru a big infidelity scandal and now his health is in question. not to mention there is this guy Rory who will stop tiger from beating jack's records. maybe i am putting the nail in tiger's coffin too soon but it sure doesn't look good. i don't think tiger will be happy unless he gets 19 major wins, from the beginning it has always been his life's goal.
michael jordan - owns NBA team and is partners in the Air Jordan Nike line. he is divorced and it is rumored he has a gambling problem and i don't doubt it at all. he just has so much money he can cover it up, not like barkley who was outed by a vegas lawsuit. but jordan is the probably the best competitor of our time, he would just not allow his team to lose. maybe the only athlete on par or above brady. it's a toss up, bobcats and air jordan vs. giselle, too close to call. although the right answer might be that pretty soon giselle could buy air jordan and the bobcats.
jay-z - married to beyonce which puts him right there with brady. owns the 40/40 club and a piece of the nj nets and has constantly re-invented himself to stay relevant. brilliant at collaboration with artists like alicia keys and mr. hudson. his only recent controversy is that in 2004 he dumped his original partner in Rock-a-Fella, Damon Dash. it was probably a great decision, dash has the biggest individual tax liens in NY & NJ totalling almost $25mm but for a rapper, disbanding your crew is worse than divorce.
howard stern - what can you say, has to be the biggest overachiever in the history of entertainment. did get divorced from his college sweetheart, Alison, and is now married to this native pittsburgh beauty 20 years his junior, beth ofstrosky:
talk about beauty and the beast, it's amazing how stern made something of nothing, what else can you say, he is winning for sure.
paul mccartney - along with lennon wrote many of the greatest songs of our time. even at 70 looks pretty good and appears to have his voice and health. lost his true north when linda died and he married that one-legged girl, Heather Mills, huge mistake, apparently she is a real psycho. Now Paul is engaged to this rich, super successful 51 year old beauty, Nancy Shevell, appears to be a very good move as everyone, including his kids, only have nice things to say about her.
i end with Billy Joel b/c I think he is the greatest American storyteller of our era (although smokey and springsteen are prolific writers, no one has the diversity and lyrical style of joel). Two of Billy's songs were recently in Hangover II (Downeaster Alexa and Allentown). But Joel truly gets no respect, in Rolling Stones 500 Best Songs of All Time, Joel is only on there once at 421 with Piano Man (that has to be the biggest screw job ever). Billy Joel's personal life has also been a mess, he had a drinking problem and suffered from severe depression, once attempting suicide by drinking furniture polish, ouch! Back in the 70's his first manager, his ex brother-in-law, stole all his dough. Probably be worth a billion if he had the advisors Paul McCartney did. Lucky to own his song catalogue (bought back and gifted to him by CBS Producer Walter Yetnikoff) because that is probably the bulk of his $160mm net worth.
But Joel is truly a paradox, wrote some of the most unbelievable love songs but is divorced 3X. His life has always been about extremes (and that's the title to one of his songs). After his first divorce, he met Christie Brinkley, Elle MacPherson (a.k.a "the body") and Whitney Houston in the Caribbean b/c he wa messing around on a piano in a lobby. It just goes to show the power of song, he dated both Elle (he was 34 and she was 19) and Christie at the same time. Would have had Whitney too but she was only 16 at the time. i guess there is no bigger turn-on for a woman than to be serenaded by love songs written for her. NONE! you could have 10 SB rings and brad pitt looks BUT fat bald joel age 62 could get any girl with his pen and piano, not even a real challenge!
In the end, winning is a state of mind and all the money and fame can't buy it. If you are truly insecure all the talent and money in the world can't cover it up. It's not a comparison game either, you will never be happy if you try to use money, athletic performance or fame as a yardstick. Life is a lot like golf, you are really not competing with everyone else, you are competing with yourself. Like golf, life is a hard game, and you rarely break par no matter how hard you try.
This post was for fun but it is more evidence that we really need FA to begin:)