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Let’s Help Macy Gray Hone her Blackjack Skills

The singer-songwriter Macy Gray is one of the most famous R&B and soul acts in America. Her raspy voice has enamored millions of listeners around the world, who have tuned in to hear her gravelly tones on tracks such as I Try. I Try is the song that catapulted Gray into international stardom as the song, which was released in 1999, won the Grammy for best female pop vocal performance in 2001 and it was nominated for both record of the year and song of the year. The same year, Gray was nominated for the best new artist award as well as the award for best female R&B vocal performance. 

In total, Gray has released 10 studio albums, with her most recent album being 2018’s Ruby. I Try is the only of Gray’s songs to have reached the Billboard Top 40, however. And, while she may not have reached such lofty chart heights as her contemporaries, other popular soul singers such as Prince, the industry does recognize her as one of the greats. Macy Gray has collaborated with the likes of Raekwon and Method Man and it was announced that she will be honored at the 7th Annual She Rocks Awards alongside Lisa Loeb and Janis Joplin.

Almost 20 years into her career, Macy Gray has admitted that she never really “planned out” her career. With this in mind, could Macy Gray be willing to consider a totally new career path? And how has she been able to last 20 years in the music industry without getting bored? We can explore the answers to this by looking at the famous soul singer’s love of blackjack and poker. 

Macy Gray’s History as a Blackjack Fan

As well as being a famous R&B and soul act, Macy Gray is one of the most well-known celebrity poker and blackjack fans as well. In fact, all the way back in 2006, Gray appeared on Bravo TV’s Celebrity Poker Showdown alongside other celebrities such as Law and Order star Christopher Meloni, the comedian and talk show host Joy Behar, and the actress Robin Tunney. Gray, who competed representing the charity Habitat for Humanity, came in a respectable third place. 

However, while she did reasonably well on Celebrity Poker Showdown, Gray’s other tries at poker and blackjack haven’t gone quite as well. Gray has said that she “loves to gamble” because it’s both “very social” and is a game that engages her brain. The singer has even won $28,000 in a single evening of playing. But despite her interest in gambling, Gray has confessed that “I’ve lost hundreds of thousands altogether. Not millions but I’ve definitely lost a lot of money – enough to go and buy myself another house.” 

Some of Gray’s previous comments about the way in which she plays poker and blackjack could offer some insight into why she has lost such a large sum of money while playing. In particular, her lack of focus could be a reason why she tends to lose a lot. Gray explains that, when she plays in Las Vegas, she just “loses” her mind. Perhaps the fact that she becomes so engrossed in the game prevents her from playing tactically. Gray may also have very little time in which to practice and hone her poker and blackjack playing skills. While a 2007 interview confirms that she regularly attends a poker tournament which takes place every other Friday night in Los Angeles, her extensive touring schedule may prevent her from regularly playing and thus improving her game. If Gray had more time or if she was able to play poker on a more regular basis (weekly or even every single day) then she may be better equipped with the tactics and strategies that she needs in order to beat out her opponents.

How Macy Can Improve Her Game

Other than “focusing more” and “trying to find more time to practice” (both of which are good pieces of advice), it would be in Macy Gray’s best interests to just work on some strategies. Even if she’s too tired or too jetlagged to practice or is halfway across the world and is unable to attend that semi-regular poker game, using certain strategies would still give her the edge during the moments that the soul singer is actually able to play. 

Some of the best winning blackjack strategies include tactics such as the decision to always double down on a hard 11. Even if you have limited blackjack knowledge, it’s worth knowing that a hard 11 is one of the most powerful hands in the game and there’s a good chance that if you double down in this scenario, you will win more money.

Other useful strategies include knowing when (or when not) to split. Splitting in blackjack is when you have the option to split your hand of two cards into two separate decks, thus giving you another opportunity to potentially beat the dealer on the other side of the table. You can only do this when you have been dealt two cards of the same value (for example, when you’ve been dealt two 8s). But there are certain pairs that should be split more frequently than others, such as a pair of 8s or a pair of Aces, because a pair of these cards makes you an underdog but splitting them makes you less of one. On the other hand, you should never split a pair of 5s or a pair of tens, with a pair of 10s being a more likely winning hand. 

Even if Macy Gray is unable to spend much time studying the games of blackjack, she could at least try to memorize the strategies detailed above. During long flights to the next tour stop, she could try to go over them or she could even play online blackjack or challenge her team members to a game. 

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