16 Music Videos Starring Oscar-Winning Actresses

Sure, we all know Angelina Jolie won an Oscar for Girl, Interrupted, or that Halle Berry made history Oscar history when she became the first African American to win a Best Actress trophy (for Monster’s Ball). But did you know that Angelina and Halle respectively starred in videos by… Meat Loaf and Limp Bizkit?

In honor of this weekend’s Academy Awards, here’s a look back at 16 music video cameos by Oscar-winning actresses. For some, these videos were career stepping-stones, or mere detours; for others, they were career lows. But all of them are recommended viewing.

And click here for complete Oscars coverage, and download the Yahoo App for instant insider updates.

16. Mecano, “La Fuerza del Destino” (starring Penelope Cruz, 1989)

No one could have predicted when 15-year-old Penelope made her acting debut, in this 1989 Spanish pop video, that she’d win a Best Supporting Actress Oscar 19 years later for her role in Vicky Cristina Barcelona. Incidentally, Mecano broke up in 1992.

15. Parachute, “The Mess I Made” (starring Jennifer Lawrence, 2009)

Silver Linings Playbook Best Actress winner J.Law was a total unknown when she starred in the 2009 video by these Virginia pop-rockers. Parachute frontman Will Anderson later told TeenMusic.com: “She was amazing… We could tell when we met her that she was going places. Here was this amazingly talented actress, and just an incredible person who also happened to be gorgeous. How could we not ask her to be in the video? Seeing her get nominated for the Oscar was amazing. No one deserves it more than her and it’s awesome to see her getting casted in such rad roles!”

14. Limp Bizkit, “Behind Blue Eyes” (starring Halle Berry, 2003)

Halle made some major career mistakes following her Best Actress win for 2001’s Monster’s Ball. And making out onscreen with Fred Durst, in a video for a terrible Who cover from the Gothika soundtrack, may have been her biggest misstep — even if Durst, who directed the clip, told MTV it was “the greatest kiss you’ll ever see.” A decade later, this admittedly makes for fascinating viewing.

13. Robbie Williams, “Something Stupid” (starring Nicole Kidman, 2001)

Robbie’s 2001 album of standards, Swing When You’re Winning, featured duets with Rupert Everett, Jane Horrocks, and Jon Lovitz, but its centerpiece was this adorable collaboration with Nicole — who’d win a Best Actress Oscar a year later for The Hours. Nicole held her own against the British pop star, which makes us wonder, when is her album coming out?

12. iRAWniQ’s “ALIENPU$” (starring Tatum O’Neal, 2014)

Tatum holds the record as the youngest thespian to win a competitive Oscar (she won the Best Supporting Actress award in 1973, at age 10, for her role in Paper Moon). The former child star has had her career ups and downs, but has continued to take on challenging roles. Case in point: This dazzling 2014 clip, in which she danced alongside an “alien Rosa Parks” played by rapper iRAWniQ. Tatum even dissected the bizarre, JB Ghuman Jr.-directed video in a play-by-play article for Vice.

11. Roy Orbison, “I Drove All Night” (starring Jennifer Connelly, 1992)

This video starred not only the A Beautiful Mind Best Supporting Actress Oscar-winner, but also Beverly Hills, 90210 heartthrob Jason Priestley. It’s a true ’90s classic if there ever was one.

10. Dave Matthews Band, “Dreamgirl” (starring Julia Roberts, 2005)

The Erin Brockovich Oscar-winner and longtime DMB fan made her music video debut in this Alice in Wonderland-meets-Fringe clip; it was first acting job after giving birth to her twins. “I just need the work,” Julia joked to People magazine at the time of the video’s release. Dave Matthews added, “We thought we’d politely give her a hand up.”

9. Renee Zellweger with Ewan McGregor, “Here’s to Love” (2003)

The Cold Mountain Best Supporting Actress winner showed off an entirely different side of herself in this playful ode to the great cinematic era of Doris Day and Rock Hudson, from the retro rom-com Down With Love. Here’s to Renee!

8. David Bowie, “The Next Day” (starring Marion Cotillard, 2013)

Marion, who was nominated last year for Two Days, One Night, displayed her own musical chops portraying Edith Piaf in 2007’s La Vie en Rose, for which she won a Best Actress Oscar. She has concurrently pursued a musical career; two years ago, she premiered an artsy collaboration with John Cameron Mitchell, Villaine, and Metronomy’s Joseph Mount titled “Snapshot of L.A.“ But her best music video cameo was in this controversial, banned-from-YouTube Bowie clip, in which she played a stigmata-stricken prostitute cavorting in a church brothel with a wayward priest played by Gary Oldman. This video definitely deserved an R rating!

7. Tom Petty, “Into the Great Wide Open” (starring Faye Dunaway, 1991)

The Network Oscar-winner joined an all-star cast that included Johnny Depp, Chynna Phillips, and, um, Richard Grieco to play an evil rock ‘n’ roll Svengali. It was clearly the role Faye was born to play. Just call this one Manager Dearest.

6. Devendra Banhart, “Carmensita” (starring Natalie Portman, 2007)

Back before she was a crazy Black Swan, Natalie was dancing in this crazy, Bollywood-inspired video by the eccentric singer-songwriter, who soon became her boyfriend. The relationship didn’t last; maybe Natalie was jealous that Devendra almost looked as pretty in sparkly Bollywood makeup as she did.

5. Brandon Flowers, “Crossfire” (starring Charlize Theron, 2010)

This badass, action-packed video, in which the Monster actress rescued the Killers frontman from ninja kidnappers, was soooo much better than Aeon Flux.

4. Meat Loaf, “Rock ‘N’ Roll Dreams Come Through” (starring Angelina Jolie, 1993)

The Girl, Interrupted Oscar-winner has also made appearances in music videos by the Rolling Stones, Lenny Kravitz, Korn, and the Lemonheads. But her most epic (and cinematic) music video appearance of all? The one in which she co-starred with Meat Loaf and played a teen runaway, of course!

3. David Bowie, “The Stars Are Out Tonight” (starring Tilda Swinton, 2013)

In a bit of inspired casting on the part of director Floria Sigismondi, this video by the late Thin White Duke co-starred thin white duchess Tilda Swinton as his dutiful wife. For years, the uncanny resemblance between Bowie and the Oscar-winning actress had been noted by observers — so much so that an entire Tumblr site was devoted to their separated-at-birth similarity. In 2003, fashion photographer Craig McDean orchestrated a shoot with Tilda during which she dressed up as Bowie, and in 2012, Hint Fashion magazine even published a rather convincing compare-and-contrast blogpost titled “Visual Proof That David Bowie and Tilda Swinton Are the Same Person.” The fact that Bowie and Tilda appeared onscreen on the same time here refuted Hint’s theory, of course.

2. Tom Petty, “Mary Jane’s Last Dance” (starring Kim Basigner, 1994)

Ah, the creepy “love story” between a morgue assistant and the beautiful dead girl of his dreams. We’re still trying to decide who’s the better actor here: Kim, or Tom himself.

1. The Rolling Stones, “Like a Rolling Stone” (starring Patricia Arquette, 1996)

Patricia won Best Supporting Actress last year for Boyhood, and gave one of the most memorable acceptance speeches in years. Also memorable? Her harrowing depiction of a strung-out party girl in this Michel Gondry-directed, fisheye-lensed clip for the Stones’ fantastic Dylan cover.

Follow Lyndsey on Twitter, Instagram, Facebook, Google+, Amazon, Tumblr, Vine, Spotify