Though no particularly active as an activist, Holly Woodlawn should be remembered as a a pioneer of the transgender community. Visibility and maintaining that visibility is one of the key components in progressing the interests and validity of the transgendered community. As one of the first openly transgendered actresses to achieve some level of fame, Holly Woodlawn paved the way for future transgendered performers to succeed in areas where previously they were shunned.
Woodlawn is best known as the subject of the song "Walk on the Wild Side." She appeared in low- budget experimental films with other transgendered actors and would set the stage for a new movement in satirical women's liberation film as a strong, confident person. She was also a successful cabaret artist with her own glitzy look..In recent years, there have been many transgendered celebrities emulating Woodlawn's style - and with large-scale acceptance.
While she certainly broke a lot of ground for transgender performers, I am not sure I would consider her a pioneer for the community. There are earlier notable figures (though not actors) such as Angela Morley or Jan Morris. She was an important member of the community, certainly, but I am not sure that I would use the word "pioneer" to describe her.
There is a rich transgender history dating back to the 1800's where a man was originally born a woman in 1829, lived as a man for 60 years, was placed in an insane asylum, yet was still able to marry a woman. There were also several soldiers in the American Civil War who were born women, but lived as men throughout their lives. On the note of famous people, there was an American Jazz musician and bandleader who was born as a woman in 1914, yet lived his lifed as a man from 1940 on, even without his own son knowing he was originally a woman. So, I would not consider Holly Woodlawn a pioneer of the transgender community, a member yes, but not a pioneer.