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ZEN ART IS SPIRITUAL art in its purest sense.  It was done not by professional artists, but by Zen monks and nuns who spent extremely disciplined lives of meditation, in a search for enlightenment and awakening to the true nature of reality.  That they were painting from their own personal knowledge of this reality, rather than from doctrines handed down, is the very foundation of this art-form's compelling power.  It is believed in Japan that the character and spiritual realization of the monk or nun are transmitted into the painting itself.
In 1707, a young monk named Hakuin saw the rustic calligraphy of an old Zen master that greatly moved him.  Although his own calligraphy may have looked more polished because of his intensive brushwork practice, it was painfully obvious to him that his work did not reflect inner realization.  Hakuin saw that in the calligraphy of the old master:
The virtue shines—skill is not important.
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He burned his brushes, redoubled his efforts in Zen practice, and did not seriously begin calligraphy again for another forty years.  All Zen art grows out of just such a tradition:  years of discipline and meditation, the quest for awakening and enlightenment.  Zen art remains a living tradition to this day, although it has strong and deep roots in the past.
The Enso, or Zen circle, is one of the most appealing themes in Zen art. The Enso itself is a universal symbol of wholeness and completion, and the cyclical nature of existence, as well as a visual manifestation of the Heart Sutra, "Form is void and void is form." One can see in these paintings of the Enso that form and void are also interdependent and, in fact, define each other. Most examples of Enso also include calligraphy, which gives further clues and refinements of meaning.

Perhaps the simplest and most straightforward of the examples shown here was done by Yamada Reirin (died 1970s):

A circle becomes like the Universe! (Figure 1)
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The earliest example shown is by Ranzan Shoryu (1718-1797). From the time he was quite young, he had a strong desire to become a monk, and he studied under some of the most influential teachers of his day. Ranzan was known for his teaching and compassion. He was a great help of the people during the Temmei famine. His Enso says:

The Universe lingers;
I bow my head. (Figure 2)
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Not all interesting works are by well-known people. This next example is a case in point. Nothing is known of this monk's history except his name and the name of his former temple. It does, however, illustrate that Zen paintings were often signed with the age of the painter. They were often of quite advanced age as Zen art was usually done after retirement. One often becomes aware when comparing paintings done by the same monk at various ages of how their Zen realization seemed to deepen with time. Toya (probably in the 1860s) tells us:

All the wise ones of the ten directions
have entered this!

Brushed by the 76 year old fellow Toya,
formerly of Shinkutsuji. (Figure 3)
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One technique of meditation is to sit, watching one's thoughts, and then after the thoughts have disappeared, through quieting the mind and body, watching the emptiness. Perhaps this is what Kankei Jomin (1876-1934) means by the calligraphy on his Enso:

Arouse the mind without letting it settle
anywhere! (Figure 4)

This composition, with the words a sharp horizontal counterpoint to the rich fullness of the Enso, is the format he preferred.
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These paintings were done as a type of moving meditation, so therefore unlike conventional artists who strive for variety and originality, these artists brushed the same subjects over and over, using the same pattern strokes. The paintings showed not only the spiritual quality of the artist, but the uniqueness of each moment in time as well. So each one is different, even though done by the same person moments apart.

The Enso is also the shape of the moon, and many Enso, as in this painting by Mannei (1790-1860), use this imagery:

Who can say my heart is like the
Autumn moon? (Figure 5)
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The painting by Taikyu (died circa 1945) of a monkey reaching for the moon on the water also contains a tiny Enso with a larger theme:

The monkey seeks the moon in the water,
chasing after it ceaselessly until death.
If instead, it sinks its hand into the deep spring
the clear, pure moonlight will illume
the universe. (Figure 6)
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Enso are most often empty inside. Because of this, the messages inside these last two examples seem even more emphasized. From Nantembo (1839-1925) comes:

Within the spinning circle of life we are born.
The human heart too should always be kep
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The final example, by Isan Shinko (1740-1815), contains at the center the character for heart:

Keep yourself firmly centered inside here
and nothing will be able to shatter you. (Figure 8)
Zen art often combines words and pictures in a way designed to give us hints of deeper meanings. Perhaps this quote of the enlightenment experience of Omori Roshi will give some additional clues about the real meaning of this Enso's symbolism:

"At the right time, you will be able to break through to the state of nothingness. You will attain this realization because of some thing and you will know with your entire being that you are at the center of absolute nothingness, at the center of an infinite circle. To be at the center of an infinite circle in this human form is to be Buddha himself. You have been saved from the beginning. You will know all these things with certainty."

While I much admire the fact that these monks and nuns devoted their lives to searching for truth of the nature of existence, few of us are called to that particularly arduous path. With these ink traces as guides for us, I believe there is much to be gained by simply viewing them and opening ourselves to that experience—visually, intellectually, and, as these paintings tells us, most importantly from our hearts.