As a teenager he hopped freight trains across the country[2] and learned tattooing from a man named "Big Mike" from Palmer, Alaska, originally using the hand-poke method.

In the late 1920s he met Gib "Tatts" Thomas from Chicago who taught him how to use a tattoo machine.

[10][11] Since 2015, an annual independently-produced event has taken place in June, called the Sailor Jerry Festival, to honor Collins' legacy in Honolulu's Chinatown.

Sailor Jerry wanted at least one of three protégés/friends – Ed Hardy, Mike Malone, or Zeke Owen – to take over his shop (or else burn it) when he died.

[16] In 1999, Ed Hardy and Mike Malone partnered with Steven Grasse from the Philadelphia-based creative agency, Quaker City Mercantile, to establish Sailor Jerry Ltd.[17][18] The limited company, which owns the commercial rights to Collins' letters, art, and flash, uses his designs on clothing and items such as ash trays, sneakers, playing cards, churchkeys and shot glasses.

As the bottle is emptied, additional pin-up girls designed by Sailor Jerry are visible on the inner side of the label.

[1][19] She was paid $20,000 for his shop and its contents in 1973 but disputed whether this sale included intellectual property or personality rights.

[20] Collins played the saxophone in a dance band and frequently hosted his own radio show, where he was known as "Old Ironsides".