Though from watching his interviews I would assume that his ascendant is in the first degrees of Virgo, I’m going to go with his official chart since on Astro.com it has an AA rating.

That makes Leonardo a Libra ascendant. It means that he’s relationship-oriented individual which is also confirmed by the conjunction of his Sun with Venus. This means that he will try to adjust his behavior and appearance to more appeal to others.

Yet in the core he may remain unchanged because we find Capricorn on the cusp of the fourth. Its ruler is in the tenth house, in Cancer, which further confirms his fixity of the beliefs he grew up with. This kind of placement also indicates a difficult childhood which caused his low self-esteem (Moon square Saturn), respect for his family roots and traditions, and interest in history.

So in the core he is a very fixed person yet he can change his outer personality to appeal to people. Also, since Pluto is located in his first house, it’s an indication of the potential to completely transform his personality and this can take place through relationships (Libra).

We can see the Moon-Pluto conjunction. This indicates a controlling mother and uncontrollable emotional and unconscious impulses. The dark side is accessible to him yet he may not be willing to deal with it. As long as he’s not willing to face it in its whole, he will continue pushing it away through escapist actions, like some habitual behavior which makes him feel good.

But that internal darkness will always be very close no matter what he does; because in this life he’s supposed to purge all the negative content of his subconscious, such as sexual addictions, traumatic experiences and deep insecurities.

Emotional trauma (Moon-Pluto conjunction) was caused by family members or some father figure at work. It caused his low self-esteem. He may be working very hard to prove his worth to the world. That could be what made him an excellent actor.

He likes emotional intensity that relationships give and that’s one of the reasons he had so many of them (from what I’ve read). He also may be gravitating towards a possible transformation of self through relationships yet I don’t think it happened so far, because he’s still not in a stable relationship.

Pluto in the first house asks him to face the death of his old personality so that a better version of himself could arise. But that would mean giving away something he is familiar with so deeply. So it can be as scary as death. But if he’s willing to do that, he would emerge a truly caring individual with healthy emotions who is able to have a stable and loving relationship.

As long as this hasn’t happened, he may be prone to deep depressions (Saturn in Cancer squaring the Moon in the first house). His mood may especially be negatively affected by family problems and problems at work, like his movies not performing well. His emotions can also take him to dark places (Moon-Pluto conjunction).

Looking further at his first house, we find a tight Mercury–Uranus conjunction at the 29th degree of Libra. This anaretic degree of Libra can give sudden starts and endings of relationships and it’s associated with divorce. He is highly advised against quickly jumping into relationships because such a start doesn’t promise a good outcome.

This particular placement also means that he is seeking freedom, especially the freedom of thought, in relationships, and that he may be very indecisive, always doubting which option to choose; and then when one option is chosen, at the last minute he could change his mind and choose something totally different.

The first quarter of his chart is busy, making his personality strong and it also indicates that he’s very resourceful. His early experiences formed his personality and made his strong enough to face the tough Hollywood industry.

Together with Capricorn Nadir, this is the signature of a resilient and resourceful person with a personality to survive disasters. I think that such traits are well-reflected in the kind of movies that he chooses also.

Saturn in the tenth house is in its own place, yet placed in an unsuitable sign. This means delay in having a family or having no family (even more so confirmed by the Capricorn Nadir). It indicates obstacles in having his own family and problems with his parents. He may have no desire to have a family unit or if he does, he may be put off by the responsibilities that it would entail or the problems that would come with it.

However, since Saturn is in the tenth house, this also means that although he may face many challenges at work that would lower his self-esteem (especially some father figure traumatizing him), with perseverance he can achieve great heights. And indeed he did – at the age of 45 he’s getting better and better at what he does, with wide acclaim. Yet for sure he had to sacrifice a lot to be where he is now – because Saturn doesn’t give gifts easily.

Let’s now discuss his second house. With three personal planets there and considering their natures and aspects, it makes him able to earn a lot of money. He loves beauty and when he likes something, he wants to own it, women including.

He may consider his partners as personal property and may even think that he owns them once the relationship is over. He is attached to beautiful things that he owns. He may be dating good-looking women because this makes him feel good about himself.

This kind of combination also means that he works hard to develop his skill set because this makes him feel secure and he likes the acknowledgement he receives for his good skills. He also may feel much better about himself if he earns a lot, and his self-esteem may go down if there’s less money.

He’s a big earner but he’s also a big spender, though his expenditures benefit him. He is attracted to well-off partners who end up benefiting him financially. He may also inherit money or other items from some partners. Business partnerships financially benefit too, and those benefits can last a long time.

Neptune in Sagittarius in the third house makes him a natural actor. He is so attuned to the environment and the people around him that it’s easy for him to become like them. The danger here is that because of his sensitivity to people and environments, if he finds himself in negative conditions, he can unconsciously take in the evil that he’s faced with.

This particular placement can create difficulty in maintaining boundaries with other people. It makes him a very sensitive and creative person. He may love humanity as a whole and can find it difficult to commit to only one person. This is the signature of a philanthropist, someone who has compassion for the misfortunes of humanity and tries to do something about it.

Leonardo has Lilith conjunct Jupiter in the sixth house. This can make him transmit magnified sexual energy through his work naturally, which is beneficial for an actor. But the higher level of this placement, considering the Pisces background, can make him a spiritual healer and someone who greatly benefits mankind through his service and gains great opportunities as a result.

This placement shows that he has a lot to give and that daily work could be the closest thing to spirituality that he experiences. Acting indeed is very suitable for him as this placement can indicate something very creative or spiritual done on a daily basis. Conventional jobs are not for him.

I’ve already discussed some things about his relationships. The seventh house gives more information. Since it’s in Aries and its ruler is located in the second house, this means that indeed he may go for younger women because he likes that energy. Aries represents young energy.

The ruler of the seventh house is located in Scorpio. This makes him attracted to sexual, energetic and competitive women. They may also be somewhat impulsive, resourceful, career-oriented and passionate.

The eighth house shows that he is able to employ and use the resources (including money) of other people and benefit himself financially from doing that. For example, he may use the ideas of other people with great success, or he may be able to spot talents in people and put them to profitable use.

He may be attracted to visit certain countries because they offer some learning opportunity or an opportunity to develop some exciting relationship. (ninth house ruler in the first house in Libra, conjunct Uranus.)

His friends are famous, creative and optimistic (Leo on the cusp of the eleventh). His friendships can be stable and long-lasting (Sun trine Saturn). They financially benefit him and the more social Leonardo is, the more he can earn (the ruler of the eleventh in the second house).

Finally, the ruler of his twelfth house is in the first, even more strengthening the need to address the subconscious in order to transform the personality. There’s a lot that’s going on in his subconscious – he may have not dealt with many fears, traumas and other darkness which make him do things habitually. He may be pushing away this call for transformation out of fear of facing the unknown and because he may be afraid to destroy his old personality.

Yet as long as this isn’t done, old dark impulses will remain, controlling his life.

I sincerely hope that he finds the courage to face all the darkness that’s just beyond the surface. Because once it’s processed and purged, a new, much more caring and harmonious personality will emerge, and all the destructive habits and impulses will be no more, opening him up to the life with much more meaning and purpose.