2000 HBO Movie - Amazon DVD Link
There are only a few movies that will guarantee me a laugh and damp eye every time I watch. One is “The Last of the Blonde Bombshells”. It is an HBO movie from 2000 with a well played crossdressing character. This movie is about getting older, reconnecting, and feelings. Well worth watching plus it portrays being transgender is a positive setting. I hope you have seen it.
Here is a well stated review from IMBd:
Dench Brings a WWII Jazz Swing Band Back Together
Much to her adult children's chagrin & nearly immediately after Elizabeth's (Dame Judy Dench) husband's death, the widowed, attic tenor saxophone player becomes bent upon openly returning to her musical hobby. Now that George is dead, Elizabeth no longer has to practice playing sax in the attic. As she grows more pleased with playing in the open, Elizabeth takes a stroll along memory lane, remembering when she was a 15 year old member of a jazz swing band, "The Blonde Bombshells": supposedly, an all-girl WWII group of talented jazz swing musicians. One of the "Blonde Bombshells'" band members was a womanizing, cross-dressing drummer, Patrick (Ian Holm), with whom Elizabeth remained friends.
Both Patrick & Elizabeth's 12-year-old grand-daughter, Joanna (Millie Findlay), press Elizabeth to round up the former band members & take up performing together again; this time as a bunch of sexagenarians. Among the band members she finds are the (still foxy!) bass playing, Madeleine (Leslie Caron); Dinah (Olympia Dukakis), a trumpet playing, alcoholic & out-spoken, money-grubbing divorcée & widow living off of wealth from her many (ex)marriages in a Craigievar Scottish castle; Gwen, (real life US star jazz singer, Clio Laine), having at the lead vocal; Annie, (June Whitfield), as the Salvation Army trombone player; Betty, (the late piano player, Joan Sims), who's located training the ivory keys in a Hastings pub.
As Elizabeth, Patrick & Joanna scout the world for members of the 1940's band & try to convince them to resume performing together, Elizabeth is oft times beside herself as she learns more than she wants to know about their adult lives--including her own--while having a blast playing terrific music with the last of the living 'Blonde Bombshells'.
Amusing, nostalgic, historical, sentimental, multi-generational entertainment that is seriously fun. The actors deliver wonderful performances. Regardless of their ages, they are still Bombshell entertainers who put on quite a show. (The DVD is now out & worth owning because of the bonus features & Dolby Digital sound). Surely as a fan of any of these terrific actors the VHS is a collector's item.