Kawakami was born in present-day Hakata-ku, Fukuoka on the island of Kyushu, "the second son of a second son" of a merchant family.:p54 At age eleven his mother died, and when he didn't get along with his stepmother he stowed away on a cargo ship to Osaka.:p54
Taking odd jobs to support himself, at eighteen he became a policeman in Kyoto.:p54 "Shortly after that, fired by the political turmoil and the strident calls for democracy, he had joined Itagaki Taisuke's Liberal party (Liberal Party of Japan (1881)) as a radical, rabble-rousing soshi agitator.....Soon his scurrilous tongue and subversive speeches were getting him into trouble. He was arrested time and time again- a hundred and eighty times in all, he bragged. At nineteen he was banned from speaking in public in Kyoto for a year and from using the name Liberty Kid. He also went to prison six times.":pp54-55
Kawakami was inspired to start his own acting troupe after receiving acting training under a rakugo master :p55 and after seeing the shosei shibai ("student theater" or "amateur theater") of fellow activist Sadanori Sudo, which "aimed at being realistic, just like in the West, and thus could claim to be following government directives to be as Western as possible in every possible way. … Far from being career-driven professionals, like the kabuki actors, they portrayed themselves as romantic, devil-may-care bohemians. Their amateur status freed them from all the constraints and conventions of the traditional theater.":pp55-56 Under the influence of philosopher Chomin Nakae, Kawakami began staging theatre productions as an outlet for his political views.
In 1888, Kawakami developed a satirical song that would make him famous. At the end of his troupe's play "The true story of our Itagaki's disaster" (based on a failed 1882 assassination of the aforementioned Itagaki) "a lone figure wearing a jaunty white headband swaggered out and with a flourish knelt in macho samurai-style, his knees spread wide apart, in front of a gold leaf screen...He was wearing a red samurai surcoat with exaggerated pointed shoulders above a plaid men's kimono....Flourishing a black fan emblazoned with a red rising sun...while a rhythmic shamisen strummed, he spat out the words in a husky rapid-fire patter, improvising verses as he went along. He sneered at the government, the rich, and the kind of people who dressed in Western clothes, aped Western ways, and spent all their money on geisha....The catchy chorus--'Oppekepe'-imitated the sound of a bugle or a trumpet:
In these days when the price of rice is rising,
You completely ignore the plight of the poor.
Covering your eyes with tall hats,
Wearing gold rings and watches,
You bow to men of influence and position
And spend your money on geisha and entertainers. …
If you think you can get to Paradise
By … using a bribe when you encounter
The King of Hades in hell, you'll never make it!
Oppekeppe, oppekepeppo, peppoppo.:pp52-53