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With only five days left before Madonna turns 50 on August 16, our birthday countdown of the 50 biggest moments in Madonna history is halfway complete. Enjoy moments 26 through 30 today, and keep coming back all week long to see what other half-century Madge milestones made her big b-day list.

26) Sean Penn Makes An Honest Woman Out Of Madonna
When Madonna met Sean Penn on the set of her "Material Girl" video, they couldn't have seemed more mismatched. He was a serious, reclusive actor who loathed the paparazzi; she was a flashy pop star whom the media hounded. When they got together, they were causing a commotion, indeed. But somehow it worked, at least for a little while, and on August 16, 1985--Madonna's 27th birthday, incidentally--the two were married after dating for less than a year. But aside from Madonna's "Live To Tell" song for Sean's film At Close Range, the Ciccone-Penn partnership was an unsuccessful one. Sean never quite got used to the flurry of paparazzi activity that followed his new wife everywhere she went--which led to him being arrested for assaulting a photographer at one point, and, according to rumor, dangling one photographer from a ninth-floor hotel balcony after the snoopy snapper sneaked into his room. And then, of course, there was Madonna and Sean's disastrous, Rotten Tomatoes-worthy onscreen collaboration, Shanghai Surprise, which in and of itself could be considered grounds for divorce. But whatever the real reason, the It Couple did officially divorce in early 1989. Later, in a touching scene in her documentary Truth Or Dare, Madge confessed that Sean was the "love of her life." Here's a clip of the paparazzi bumrushing the Ciccone-Penn wedding, which was probably a bad omen:

27) Madonna's World Domination Continues With Maverick Records
By the early '90s, some naysayers were claiming that Madonna's heyday was over--that she was a hasbeen, no longer the biggest female singer on the planet. But Madge had the last laugh in 1992, when she founded Maverick Records, the label that eventually signed Alanis Morissette. Alanis soon became the biggest non-Madonna female singer on the planet, selling 30 million copies worldwide of her album Jagged Little Pill (the third-biggest selling album by a female artist, and the biggest-selling debut album of all time). So even when Madonna was between album releases, she was still dominating the charts. Here's Madonna talking about her protégé:

28) She Discovers & Popularizes Kabbalah
Only someone like Madonna could turn Jewish mysticism into a hip Hollywood trend. When the famously lapsed Catholic became a devotee of Kabbalah in the late 1990s, suddenly starlets like Britney Spears were sporting red string Kabbalah bracelets (purchased on Robertson Blvd., of course) and hanging out at L.A.'s Kabbalah Centre as if it were a Hyde-like nightspot. For some fair-weather Kabbalah-ists, this was a fly-by-night fad--but to her credit, Madonna seems to take the religion seriously. She even donated $21 million towards a new Kabbalah school for children. However, Madonna still managed to create controversy even in this aspect of her life, when Israeli rabbis condemned the song "Isaac" from Confessions On A Dance Floor because it was supposedly a tribute to Rabbi Isaac Luria (Jewish law forbids commercializing a rabbi's name). Here's a 2004 clip of Madonna talking about how Kabbalah has influenced her music and life:

29) Madonna Plays Live 8
Bob Geldof's historical series of global charity concerts included some of the biggest pop stars of 1985: Sting, Phil Collins, U2, Queen, David Bowie, Elton John, Run-DMC, Bryan Adams, Tom Petty, the Cars, Duran Duran, Hall & Oates, etc. Madonna, a relative newcomer at the time, was therefore relegated to a mid-afternoon Live Aid timeslot. But her participation in such an event signified the arrival of a true superstar. She was playing in the big leagues now:

30) Madonna Plays Live 8
Twenty years after she appeared at Live Aid--back when she was the new kid on the block, and the new wife of Sean Penn--in 2005 Madonna was re-recruited by Bob Geldof for  Live 8, another big awareness event in London's Hyde Park. Her performance of "Like A Prayer' with Ethiopian famine survivor Birhan Weldu--who as a little starving girl served as the posterchild for Geldof's Band Aid campaign, and had now grown up to be a striking young lady--was one of the concert's most tearjerking and triumphant moments:

Come back tomorrow for Madonna moments 21-25!