I was 14 years old the first time I saw Madonna. It was 1984, the summer before my freshman year in high school, and I was in my bedroom watching an FM-102-hosted video show on my shabby 13-inch black-and-white set. The reception was poor, but even with the static and tinny sound, I was left awed. The "Borderline" video featured a young Madonna as an aspiring model torn between her hip, street friends and the glamorous, yet sometimes stifling environment of high-fashion modeling. At once, Madonna was cool and mysterious, sexy and tough. Vulnerable, yet ultimately in command. The image, especially for an awkward adolescent, was powerful. Over the next few years, along with most of my friends and millions of girls across the country, I followed Madonna Louise Ciccone's every move, buying every album, noting every fashion step and personality metamorphosis -- from funky urban dancer to polished high-society diva. By the time I reached college, Madonna-watching had taken on a new element. Feminists (traditional, neo, whatever) had been deconstructing the Material Girl ever since she first blazed across MTV with her kinetic, candy-colored videos and rapidly changing personas. From Gloria Steinem and Susan Faludi to Naomi Wolf and Camille Paglia, Madonna has provided a wealth of material as a potent figure: a woman who reached the top by ignoring the rules. But while I -- along with my friends and peers -- was ready to study Madonna in an academic setting, I was also reshaping my feminism, testing boundaries and breaking new rules. Musically and culturally, I needed someone more cynical, angrier -- ready to kick ass. Enter Courtney Love.Love, wife of Nirvana vocalist Kurt Cobain and singer-songwriter for her own band Hole, slouched onto the scene circa 1992, singing about being a "Teenage Whore" and only "Pretty on the Inside." With Madonna having long discarded her daring street fashions -- ripped stockings, exposed midriff, teased hair, crucifixes, etc. -- for more expensive tastes such as Prada and Chanel, it was easy for Love to fill the vacuum with her own ripped stockings, exposed crotch, ratty hair and baby barrettes. The obvious similarities between Madonna and Love have the press on the offensive, going for blood. Both women are outspoken, cartoonish blond icons who've redefined femininity, sexuality, motherhood and female power. Even in today's ever-widening pop culture landscape, there's barely enough room for the two of them. After hearing Love's music, Madonna tried to sign the singer to her fledgling, pre-Alanis record label, Maverick. When Love refused, signing instead with Geffen, it set the two up for a bizarre, media-fueled catfight. Madonna denied any interest in Courtney, and Courtney called Madonna washed up. But, to their credit, the two quickly bored of the power struggle. "It's not a competition. We're so different. She's so much the younger child and I'm so much the older child," Love recently told Vogue magazine. "It's like Eddie Bauer and Versace. It's a different buzz."OK, sure, but with both women currently hot in the spotlight, the media -- and the public -- can't help but take notes and compare. The respective roles played by Madonna and Courtney Love in Evita and The People vs. Larry Flynt are remarkably alike in story -- each portrays a controversial woman, tracing her steps from adolescence to early death -- and with what each singer-turned-actress brings to the part.In Evita, Madonna finally stages the role many say she was born to play: Eva Peron, the young actress wife of Argentina's nationalist leader Juan Peron. Eva, popularly known as Evita to her loyalists, is widely acknowledged for helping to secure her husband's win with head-turning glamour and glitz. Here was a once lower-class citizen promising the great unwashed masses a taste of the riches she'd married into in exchange for votes. Once in power, Peron quickly fell into disrepute, but upon her premature death from cancer, her legacy as Argentina's patron saint became larger than life.Love's character earned her own historical footnote for a similar stand-by-your-man ethic. Punk junkie Althea Leasure, wife to Hustler publisher Larry Flynt, helped push the magazine to national popularity by coupling her raw business instincts with wild sexual tastes. Throughout Flynt's numerous courtroom trials, the former stripper staunchly stood in alliance with her husband and his refusal to back down on obscenity charges. According to the film, she actually pushed him to make the sex rag sleazier. Eventually, the couple's free sex and drug lifestyle led to Althea's AIDS-related death.Both Madonna and Love have received Golden Globe nominations for their roles (Madonna for Best Actress, Love for Supporting Actress), and it's expected that each actress will snag an Oscar nod as well. Both, however, are also the subject of critical snipings that accuse them of simply playing to type.Madonna's definitely in her own element in this regard. Evita -- which maintains a surprisingly crisp pace despite its nearly three-hour run time -- is like one long music video. "Borderline," "Like a Virgin," "Material Girl" "Open Your Heart" and "La Isla Bonita" -- all of Madonna's early-to-mid-career MTV hits are reprised here. Moving seamlessly between songs, we see Evita evolve from guileless ingenue to materialistic schemer.Likewise, in Larry Flynt, Love does what she does best: talk. Her Althea is a snappy, intelligent upstart with her eye on the prize -- unaware or uncaring of what others think of her.It's easy to snicker at scenes of Evita/Madonna discarding lovers like outdated fashions and at the sight of Althea/Courtney desperately shooting smack. After all, isn't Madonna an ambitious zealot who slept her way to the top and Love just another immoral heroin junkie?Maybe, but it takes more than life experiences to be convincing on screen, and both actresses bring something deeper to their respective roles. Evita and Althea, like Madonna and Love, were similar women whose lives were largely shaped by classism and sexism, and there's a pivotal scene in each film that clearly illustrates what each actress has gone through to reach her current state of public acceptance.The moment comes midway through Evita. Scorned by the upper-class society she's married into, Eva Peron gets her sweet revenge upon Argentina's elite when she's officially welcomed with a handshake from every high hat who previously snubbed her.The same idea is played out in Larry Flynt. Althea, weak and disheveled from AIDS and drug addiction, is rebuffed by her husband's employees while he's in the hospital. Near the film's end, the employees are punished for this misbehavior by being made to shake Althea's hand. It's Flynt's loving gift to her.The scenes are both poignant moments and powerful statements about what not only the characters, but Madonna and Courtney Love have prostituted to achieve acceptance. Madonna used to be a sassy, sexy street kid; Love an unapologetically rough, fiercely independent musician. Now Madonna's gone adult contemporary with a baby and permanent rotation on VH-1 and Love's gone uptown, giving up booze and drugs and doing Vogue fashion spreads (wearing Versace and Dolce & Gabbana, no less).Still, both women, despite their obvious flaws and society's insatiable appetite for something new, remain rich cultural symbols; unconventional characters of strength feared and reviled by the status quo, admired and copied by fans. The question that remains is which woman will last. Time and time again, despite regular press reports of being "washed up," Madonna has survived: reinventing herself every couple of years in a near-seamless evolution. Through it all, she's remained in control, supervising with a tight rein the production of every product she's associated with.The jury's still out on Love. 1994's Live Through This was critically acclaimed, but her detractors have publicly aired suspicions that she didn't write -- or even play -- much of that album's music. This year's pending Celebrity Skin album might settle that particular question, but mainly it underscores the controversy that seems to follow Love wherever she goes, the idea that she's a walking disaster who may or may not have had extensive plastic surgery, used drugs during her pregnancy and aided in a cover-up regarding her husband's death.While she (and her publicists) continue to rework her image, mainstream media and trendwatchers will continue to pit her against Madonna in a pointless battle of the rock divas. Madonna's already come out on top; she's echelons above Love. Courtney Love still has a legion of battles to fight, mostly against herself.In the meantime, she's just reaping some of the rewards a little early.