Kodansha International (www.kodansha-intl.com), a Japanese publisher, has probably published more books on Japan in English -- including Japanese-language textbooks -- than any other company. Available at major bookstores in Japan, they can also be ordered online at www.amazon.com.
History -- The definitive work of Japan's history through the ages is Japan: The Story of a Nation (Alfred A. Knopf, 1991), by Edwin O. Reischauer, a former U.S. ambassador to Japan. For more recent coverage, there's A Modern History of Japan: From Tokugawa Times to the Present, by Andrew Gordon (Oxford University Press, 2003).
For an overview of Tokyo's history, refer to Edward G. Seidensticker's Low City, High City (Harvard University Press, 1991), which covers the period from 1867 to 1923, when the city rapidly grew from an isolated and ancient shogun's capital into a great modern city. Its sequel, Tokyo Rising (Harvard University Press, 1991), describes the metropolis after the Great Earthquake of 1923 and follows its remarkable development through the postwar years until the end of the 1980s. Describing the daily lives of samurai, farmers, craftsmen, merchants, courtiers, and outcasts, with a special section devoted to life in Edo, is Charles J. Dunn's fascinating Everyday Life in Traditional Japan (Tuttle, 2000).
Society -- Reischauer's The Japanese Today (Tuttle, 1993) offers a unique perspective on Japanese society, including the historical events that have shaped and influenced Japanese behavior and the role of the individual in Japanese society; an updated version is Reischauer's Japanese Today: Change and Continuity (Belknap Press, 1995). A classic description of the Japanese and their culture is found in Ruth Benedict's brilliant The Chrysanthemum and the Sword: Patterns of Japanese Culture (New American Library, 1967), first published in the 1940s but reprinted many times since. For a more contemporary approach, read Robert C. Christopher's insightful The Japanese Mind: The Goliath Explained (Linden Press/Simon & Schuster, 1983).
For a look into life in the capital -- education, employment, home life, and more -- check your school or public library for Life in Tokyo: The Way People Live (Lucent Books, 2001), by Stuart A. Kallen. More entertaining is Tabloid Tokyo: 101 Tales of Sex, Crime, and the Bizarre from Japan's Wild Weeklies (Kodansha, 2005), by Mark Schreiber, and its sequel, Tabloid Tokyo 2 (Kodansha, 2007).
Culture & the Arts -- Introduction to Japanese Culture, edited by Daniel Sosnoski (Tuttle, 1996), gives a great overview and covers major festivals, the tea ceremony, flower arranging, Kabuki, sumo, Buddha, kanji, and much more. For a historical perspective on Tokyo's cultural development through the centuries, including literature, architecture, Kabuki, and the arts, see Tokyo: A Cultural History by Stephen Mansfield (Oxford University Press, 2009).
The Japan Travel Bureau puts out nifty pocket-size illustrated booklets on things Japanese, including Eating in Japan, Living Japanese Style, Martial Arts & Sports in Japan, and Japanese Family & Culture. My favorite is Salaryman in Japan (JTB, 1986), which describes the private and working lives of Japan's army of white-collar workers who receive set salaries.
Fiction -- Tokyo bookstores have entire sections dedicated to English translations of Japan's best-known modern and contemporary authors, including Mishima Yukio, Soseki Natsume, Abe Kobo, Tanizaki Junichiro, and Nobel prize winners Kawabata Yasunari and Oe Kenzaburo. An overview of Japanese classical literature is provided in Anthology of Japanese Literature (Grove Press, 1955), edited by Donald Keene. Modern Japanese Stories: An Anthology (Tuttle, 1962), edited by Ivan Morris, introduces short stories by some of Japan's top modern writers, including Mori Ogai, Tanizaki Junichiro, Kawabata Yasunari, and Mishima Yukio.
Soseki Natsume, one of Japan's most respected novelists of the Meiji Era, writes of Tokyo and its tumultuous time of change in And Then (Putnam, 1982), translated by Norma Moore Field, and in Kokoro (Regnery Publishing, 1985), translated by Edwin McClellan. Although not well known in the West, Enchi Fumiko writes an absorbing novel about women trapped by social constraints in 19th-century Tokyo in The Waiting Years (Kodansha, 2002), first published in 1957.
Favorite writers of Japan's baby-boom generation include Murakami Ryu, who captured the undercurrent of decadent urban life in his best-selling Coin Locker Babies (Kodansha, 1995) and wrote a shocking expose of Tokyo's sex industry in In the Miso Soup (Kodansha, 2003), though its murder descriptions might be too graphic for some; and Murakami Haruki, whose writings include Dance Dance Dance (Kodansha, 1994), about a 30-something protagonist living in a glittering high-rise but searching for more meaning in life, and South of the Border, West of the Sun (Knopf, 1999), another story of a bewildered man in contemporary Tokyo.
Probably the most internationally well-known film shot in Tokyo in recent years is Sophia Coppola's Lost in Translation (2003), in which two lost characters played by Bill Murray and Scarlett Johansson find solace in each other's company as they drift through an incomprehensible -- and at times hilarious -- Tokyo.
Love and Pop (1998), by director Anno Hideaki, best known for anime films, is a low-budget film based on a novel by Murakami Ryu about "compensated dating," in which teenage girls are paid to go out with older businessmen. Another film dealing with this phenomenon rarely covered in the Western press is Harada Masato's Bounce Ko Gals (1998), which presents a shocking but heart-felt story of sexual exploitation and loss of innocence.
Adrift in Tokyo (2007), directed by Satoshi Miki, gives an up-close and personal view of Tokyo's back streets and neighborhoods as two men -- a debt collector and a university student who owes money -- walk across the city on a journey that seems aimless but provides a turning point in the lives of both men.
Other movies partly or wholly filmed in Tokyo include German writer-director Doris Dorrie's Cherry Blossoms (2008), about a middle-aged Bavarian, who, mourning the death of his wife, takes a trip to Tokyo and meets a young Butoh dancer also grieving over the death of a loved one; and Tokyo Sonata (2008), directed Kurosawa Kiyoshi, about an ordinary family in contemporary Tokyo in which the father loses his job but is too ashamed to tell his family and thus pretends he's going to work every day. Spanish director Isabel Coixet's Map of the Sounds of Tokyo (2009) centers on two star-crossed lovers in Tokyo, with rich imagery of the city's neon streets, love hotels, noodle shops, fish market, and other true-to-life scenes.