There are so many books and articles on Buddhism, meditation and spirituality available, it can sometimes seem overwhelming to know what to read. Below are some of my recommendations.
Mindfulness in Plain English by Bhante Henepola Gunaratana -- This book is a classic and is highly recommended.
Journey to the Center: A Meditation Workbook by Matthew Flickstein -- A practical guide to beginning meditation.
Buddhism Is Not What You Think by Steve Hagen -- From a different tradition, Zen, but very good.
With Each and Every Breath by Thanissaro Bhikkhu -- Offers a clear framework for a meditation practice based on the Pali suttas/discourses of the Buddha and with an emphasis on using the breath as the object of meditation.
Breath By Breath by Larry Rosenberg -- A very accessible presentation on Insight Meditation and the practices of the Discourse on Mindfulness of Breathing In and Out
And, of course, the articles by Philip Jones on this site
THE PATH OF PRACTICE:
The Four Noble Truths by Ajahn Sumedho - A short on-line book based on talks by the author.
The Noble Eightfold Path by Bhikkhu Bodhi -- An orthodox presentation of the Noble Eightfold Path, available for free.
The Meditator's Atlas by Matthew Flickstein -- A contemporary, comprehensive guide to the path of Insight Meditation practice based on the classic commentary the Visuddhimagga (The Path of Purification.) Originally published as Swallowing the River Ganges.
A Path with Heart by Jack Kornfield -- A contemporary presentation of the path of practice combining Insight Meditation with perspectives of other spiritual traditions. Includes discussions of emotional healing, integrating spiritual practice into daily life and other issues encountered on the path.
The Development of Insight by Patrick Kearney (The Path to Freedom, The Seven Purifications, and The Insight Knowledges) provides a summary of process of the path as described in the Visuddhimagga (The Path of Purification.)
The Wise Heart by Jack Kornfield -- Presents a large range of practices in the context of Buddhist psychology.
THE FOUNDATIONS OF MINDFULNESS
The books above by Flickstein and Kornfield include practice exercises or investigations from the MahaSatipatthana Sutta. The two books immediately below may include practice information but also provide commentary on the sutta. The articles in this section include commentaries, practices and other resources related to this key teaching.
The Four Foundations of Mindfulness by Venerable U Silananda -- Commentary and practice information from the Mahasi Sayadaw lineage.
satipatthana: the direct path to realization by Analayo -- A very detailed and comprehensive look at this sutta.
MahaSatipatthana Sutta (Annotated) - This sutta is presented with notes by Michael Potter from a 14-tape series of talks by Bhikkhu Bodhi.
The Nine Cemetery Contemplations - This meditation from the Satipatthana Sutta aids in breaking one's attachment to one's body and to the bodies of others. Pictures of a corpse in various stages of decomposition are provided to assist in this meditation. Warning: these pictures are not for the faint of heart.
I Know, But I Don't Know: The Contemplation of Death by Ajahn Brahmavamso
The Last Stronghold of Self by Gloria Taraniya Ambrosia -- Offers a very accessible description of coming to see the Five Aggregates as not-self.
Cultivating Choiceless Awareness by Matthew Flickstein
THE THREE CHARACTERISTICS
The Practice of Impermanence: An Interview with Joseph Goldstein - A discussion of the three universal characteristics of experience with special emphasis on impermanence.
Anatta (Not-Self) by Ajahn Brahmavamso
INVESTIGATION AND AWARENESS
Both Ajahn Sumedho and Toni Packer place a strong emphasis on investigating one's experience and resting in awareness. All of their books are recommended. Two of them are:
The Sound of Silence by Ajahn Sumedho
The Silent Question by Toni Packer
Insight Meditation is largely a wisdom practice. Yet for it to be successful, it must be balanced with lovingkindness and compassion, both towards others and ourselves.
Lovingkindness by Sharon Salzberg -- A clear presentation of the practices of lovingkindness, compassion, empathetic joy and equanimity.
Lovingkindness meditations by Ayya Khema -- Creative and highly effective approaches to this meditation.
The Four Sublime States - by Nyanaponika Thera. A series of short reflections on the development of the four brahmavihara ("sublime states" or "divine abidings": love, compassion, sympathetic joy, and equanimity) and the role they play in meditative practice.
Flickstein's two books, above, present the dominant approach to concentration in Insight Meditation in the West, the use of momentary concentration. The following works emphasize cultivating deeper states of concentration, the jhanas or meditative absorptions, as a tool for developing insight.
Focused and Fearless by Shaila Catherine. This very clear book places concentration practice within the context of the whole path of meditation. The style of writing reveals the author's own close examination and investigation of her own experience with these practices. This book is highly recommended whether or not one is interested in developing deep states of concentration.
The Experience of Samadhi by Richard Shankman
Mindfulness, Bliss and Beyond by Ajahn Brahm
Who Is My Self? by Ayya Khema
Leigh Brasington has a number of papers on the jhanas or meditative absorptions . See "Interpretations of the Jhanas" for a fairly objective survey of the different approaches to jhana practice.
The Soul in Buddhism: Mind, Karma, Rebirth and the Buddhist Middle Path Philosophy by Ajahn Punnadhammo -- Offers a very clear and succinct explanation of the Middle Way, Karma, Rebirth and Dependent Origination.
NOT-SELF & EMPTINESS
Fundamental to the Buddha's path is realizing what terms such as "not-self" and "emptiness" mean and the perspective they provide for living a life of contentment, compassion and joy.
Heartwood of the Bodhi Tree by Buddhadasa Bhikkhu -- The subtitle "The Buddha's Teaching on Voidness" perfectly describes this valuable book.
Verses from the Center by Stephen Batchelor -- A poetic translation of Nagarjuna's The Fundamental Wisdom of the Middle Way, a deep exploration of not-self or emptiness.
Trust in Mind by Mu Soeng -- A translation and commentary on the Zen poem that begins "The Great Way is not difficult for those who have no preferences."
NON-DUAL PERSPECTIVES ON THE AWAKENED LIFE
The books in the "Investigation and Awareness" and "Not-Self and Emptiness" categories could also fit in this one.
One Dharma by Joseph Goldstein -- In its later chapters, this book explores the nature of awakening and some of the differing perspectives offered within Buddhism.
"Who Looks in the Mirror?: The Nature of Consciousness" in The Wise Heart by Jack Kornfield -- Uses the analogy of light as both waves and particles to make the different views and experiences of consciousness understandable.
Small Boat, Great Mountain by Amaro Bhikkhu -- Available both in print and as a pdf, this book makes clear that Theravada Buddhism also includes the non-dual perspective of Tibetan Dzogchen practices.
"Ajahn Chah's View of 'The View'" by Ajahn Amaro - A reflection by Ajahn Amaro on the similarities between the Theravada Buddhist teachings of Ajahn Chah and the Tibetan Buddhist Dzogchen teachings.This essay is part of the booklet Broad View, Boundless Heart by Ajahn Passano and Ajahn Amaro.
Awake in the Heartland by Joan Tollifson -- A delightful presentation of non-duality using stories from the author's life along with reflections on what non-duality means in terms of an ordinary life.
Emptiness Dancing by Adyashanti -- A collection of talks by a contemporary teacher of non-duality.
No Boundary by Ken Wilber -- A more cognitive exploration of the nature of non-duality in a relatively short work.
Presence-Awareness by Sailor Bob Adamson -- A short collection of talks by one of Sri Nisargadatta's students.