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What 66 Celebrities Wore When They Won Their First Oscar

Mehera Bonner
14 min read
Dress, Clothing, Gown, Fashion, Beauty, Fashion model, Hairstyle, Shoulder, Wedding dress, Formal wear,
What Celebs Wore When They Won Their First OscarGetty Images


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The Academy Awards are coming up, and honestly all we can hope and pray for is that the presenters get everyone's names actually right this year. While there's no telling what awkwardness, red carpet fails, and live TV flubs we might be in store for—especially if John Travolta shows up, bless—one thing is certain: the fashion will be lit. Or totally atrocious. Honestly, every year is an unpredictable and exciting adventure!

Picking out the dress to wear while potentially/hopefully/please-fingers-crossed taking home a freaking gold Oscar statue is obviously a huge deal, so let's take a look back at 50 actresses who nailed their winning look—or at the very least, wore something memorable, even if it looked vaguely ??.

Vivien Leigh

The year: 1940

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The Win: Best Actress, Gone with the Wind

The Look: Vivien wore a stunning evening gown by Irene Gibbons, a famous costume designer who was a fave of Marlene Dietrich and Greta Garbo. She accessorized the look with a Van Cleef & Arpels necklace—a very chic gift from her then-fiancé Laurence Olivier.

Vivien Leigh Holds Oscar Statue
Bettmann - Getty Images

Ingrid Bergman

The Year: 1945

The Win: Best Actress, Gaslight

The Look: Damn, what a departure from the norm! Instead of an over-the-top gown, Ingrid wore a simple skirt and top with sandals. And fun fact: this movie is credited for coining the term "gaslighting" (it's about a woman whose husband convinces her she's going crazy when he's, in fact, manipulating her).

Ingrid And Oscar
Hulton Archive - Getty Images

Audrey Hepburn

The Year: 1954

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The Win: Best Actress, Roman Holiday

The Look: Audrey's delicate dress from her favorite designer Givenchy is one of the most famous Oscar gowns of all time. The cinched waist? The boat neck? The belt?! Your faves simply shouldn't even bother.

Audrey Hepburn Holding Oscar
Bettmann - Getty Images

Grace Kelly

The Year: 1955

The Win: Best Actress, The Country Girl

The Look: Vertigo costume designer Edith Head is responsible for this stunning gown, and it was said to be the most expensive Oscars dress ever at the time—it cost $4,000.

Formal wear, Hairstyle, Event, Fashion, Dress, Smile, Suit, Ceremony, Tuxedo, Wedding,
Getty Images

Elizabeth Taylor

The Year: 1961

The Win: Best Actress, Butterfield 8

The Look: Christian Dior, of course. Apparently Elizabeth's fourth husband Eddie Fisher bought this dress for her, along with “almost the entire collection.”

Fashion, Formal wear, Event, Ceremony, Cool, Wedding, Fun, Marriage, Dress, Suit,
Getty Images

Julie Andrews

The Year: 1965

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The Win: Best Actress, Mary Poppins

The Look: Julie collected her first Oscar in a pale yellow dress by an unknown designer, and I think we can all agree she looked like a knockout. Maria Von Trapp could never!

event, yellow, fun, fashion, formal wear, smile, photography, dress, suit, party,
event, yellow, fun, fashion, formal wear, smile, photography, dress, suit, party,

Goldie Hawn

The Year: 1970

The Win: Best Supporting Actress, Cactus Flower

The Look: Goldie actually wasn't around to accept her Oscar because she was busy filming a movie in London, but she showed up the next year looking next-level incredible with a flower atop her head and eyelashes that rival Bambi's.

Hair, Hairstyle, Blond, Headpiece, Eyebrow, Beauty, Hair accessory, Chin, Long hair, Lip,
Getty Images

Jane Fonda

The Year: 1972

The Win: Best Actress, Klute

The Look: Pro tip, always pair your shaggy mullet with an Yves Saint Laurent haute couture suit and purple turtleneck if you wanna get lucky.

Actress Jane Fonda at Academy Awards
Bettmann - Getty Images

Faye Dunaway

The Year: 1977

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The Win: Best Actress, Network

The Look: This Geoffrey Beene belted dress goes perfectly with Faye Dunaway's expression of "yeah, you better believe I just did the damn thing."

Faye Dunaway Attends the 1977 Oscars
Tony Korody - Getty Images

Diane Keaton

The Year: 1978

The Win: Best Actress, Annie Hall

The Look: Is this Ruth Morley blazer and skirt combo the most Diane Keaton-y outfit Diane Keaton has ever worn? I'm thinking yes.

Performance, Performing arts, Furniture, heater, Stage,
Getty Images

Maggie Smith

The Year: 1979

The Win: Best Supporting Actress, California Suite

The Look: Listen, I'm into Maggie Smith's dress and all, but I'm really here to discuss literally everything about Brooke Shields' whole lewk.

Event, Fashion, Headpiece, Fun, Hair accessory, Fashion design, Ceremony, Smile, Fawn, Performance,
Getty Images

Meryl Streep

The Year: 1980

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The Win: Best Supporting Actress, Kramer vs. Kramer

The Look: Excuse me, but how is society not constantly obsessing over the fact that Meryl Streep wore a popped collar when she won her first Oscar? French designer Pauline Trigère nailed it.

Fashion, Costume, Dress, Photography, Fashion design, Formal wear,
Getty Images

Jessica Lange

The Year: 1983

The Win: Best Supporting Actress, Tootsie

The Look: Jessica Lange looks like the Statue of Liberty in this Valentino dress, and I, for one, am here for it.

Hair, Hairstyle, Fashion, Photography, Dress,
Getty Images

Anjelica Huston

The Year: 1986

The Win: Best Supporting Actress, Prizzi's Honour

The Look: Oh, this ol' thing? Just an explosion of '80s asymmetrical goodness by Tzetzi Ganev, the vibes of which I'll be attempting to recreate this holiday season.

Hair, Shoulder, Green, Hairstyle, Dress, Arm, Smile, Joint, Gown, Long hair,
Getty Images

Jodie Foster

The Year: 1989

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The Win: Best Actress, The Accused

The Look: A periwinkle off-the-rack dress that your mom probably wore to prom. Also, ARE THOSE NUDE STOCKINGS?

Dress, Fashion, Cocktail dress, Leg, Shoulder, Award, Carpet, Event, Red carpet, Long hair,
Getty Images

Emma Thompson

The Year: 1993

The Win: Best Actress, Howards End

The Look: Emma wore this cute Caroline Charles gown, and apparently Valentino claimed she'd "settled" by not picking a couture designer. Please give me a moment while my eyes un-roll from my head, thx.

Clothing, Dress, Gown, Fashion, Formal wear, Haute couture, Flooring, Costume, Style, Statue,
Getty Images

Marisa Tomei

The Year: 1993

The Win: Best Supporting Actress, My Cousin Vinny

The Look: No one expected Marisa to take home the win, but she stole the spotlight in a Chanel gown with black piping and full-length gloves—which had kinda similar vibes to Julia Roberts' Valentino Oscars dress (coming up in a few).

Dress, Formal wear, Event, Fashion, Ceremony, Premiere, Gown, Carpet, Suit, Flooring,
Getty Images

Holly Hunter

The Year: 1994

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The Win: Best Actress, The Piano

The Dress: Holly Hunter's dress is as classically Vera Wang as it gets, and I want it in my wardrobe ASAP in case anyone's feeling generous.

Award, Trophy, Event, Flooring,
Getty Images

Susan Sarandon

The Year: 1996

The Win: Best Actress, Dead Man Walking

The Look: Wow, this is...a lot! For reasons that remain confusing more than 20 years later, Susan Sarandon paired her bronze Dolce & Gabbana ballgown with a bronze shawl, bronze hair, and bronze rimmed sunglasses. Okay!

Fashion, Hairstyle, Dress, Costume design, Victorian fashion, Costume, Fashion design, Carpet, Gown, Kimono,
Getty Images

Juliette Binoche

The Year: 1997

The Win: Best Supporting Actress, The English Patient

The Look: Attention @ The Academy. If I ever win an Oscar, I, too, will show up looking like a cross between the evil queen in Snow White and any given vampire. Thanks for your time.

Clothing, Fashion model, Outerwear, Fashion, Formal wear, Dress, Coat, Overcoat, Costume design,
Getty Images

Helen Hunt

The Year: 1998

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The Win: Best Actress, As Good as It Gets

The Look: Not sure how I feel about the match-y shoes, but Helen Hunt's ice blue Tom Ford for Gucci gown holds TF up.

Dress, Floral design, Flower Arranging, Gown, Event, Formal wear, Floristry, Flower, Plant, Ceremony,
Getty Images

Kim Basinger

The Year: 1998

The Win: Best Supporting Actress, L.A. Confidential

The Look: Things I would happily wear to work if people would LET ME: this mint-green Escada gown.

Dress, Standing, Shoulder, Hairstyle, Flooring, Fashion, Gown, Carpet, Blond, Haute couture,
Getty Images

Gwyneth Paltrow

The Year: 1999

The Win: Best Actress, Shakespeare in Love

The Look: Love it or hate it, Gwyneth Paltrow's baby pink Ralph Lauren princess gown is maybe the most recognizable Oscars dress of all time. Other than the dress she wore the next year with no bra, of course.

Dress, Gown, Clothing, Fashion, Formal wear, Shoulder, Carpet, Haute couture, Event, Flooring,
Getty Images

Angelina Jolie

The Year: 2000

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The Win: Best Supporting Actress, Girl, Interrupted

The Look: Speaking of people looking like vampires, allow me to present Angelina Jolie in this floor-length gown by Versace. Would happily let her suck my blood.

Red carpet, Carpet, Premiere, Red, Flooring, Event, Dress, Suit, Formal wear, Tuxedo,
Getty Images

Hilary Swank

The Year: 2000

The Win: Best Actress, Boys Don't Cry

The Look: I mean, this Randolph Duke ballgown isn't the best dress of all time, but it accomplished its job of showing off that truly massive diamond necklace.

Dress, Fashion model, Performance, Fashion, Singer, Gown, Event, Textile, Fashion design, Gesture,
Getty Images

Julia Roberts

The Year: 2001

The Win: Best Actress, Erin Brockovich

The Dress: Julia chose to wear a 1992 Valentino couture dress to take home her win, and she's saving it for her daughter Hazel. "It’s under my bed, in a box," she told People. "I have this little space in my house that my husband refers to as the heritage collection. Things I go, 'I can’t get rid of [this], what about Hazel?'"

Clothing, Dress, Red carpet, Carpet, Gown, Fashion, Flooring, Formal wear, Shoulder, Event,
Getty Images

Halle Berry

The Year: 2002

The Win: Best Actress, Monster's Ball

The Look: Does anyone else remember watching Halle Berry take the stage for her historic Oscars win? She could have worn literally anything and looked amazing, but this Elie Saab gown was a glorious choice.

Hairstyle, Dress, Formal wear, Photography, Gown, Carpet, Performance, Flooring,
Getty Images

Jennifer Connelly

The Year: 2002

The Win: Best Supporting Actress, A Beautiful Mind

The Look: Like, would I have paired my nude Balenciaga dress with a skinny yellow scarf? No. But do I have an Oscar? Also no.

The 74th Annual Academy Awards - Press Room
SGranitz

Catherine Zeta-Jones

The Year: 2003

The Win: Best Supporting Actress, Chicago

The Look: Catherine Zeta-Jones was nine (NINE!) months pregnant at the Oscars, and wow, Versace came through with her maternity dress.

Yellow, Dress, Beauty, Gown, Formal wear, Shoulder, Red carpet, Carpet, Fashion, Statue,
Getty Images

Nicole Kidman

The Year: 2003

The Win: Best Actress, The Hours

The Look: Nicole Kidman's Grace Kelly vibes are so strong in this Jean Paul Gaultier dress, I'm now convinced time travel is real.

Dress, Jewellery, One-piece garment, Day dress, Waist, Costume design, Makeover, Gown, Vintage clothing, Cocktail dress,
Getty Images

Charlize Theron

The Year: 2004

The Win: Best Actress, Monster

The Look: The pose, the Old Hollywood waves, the sparkles, the Gucci gown, the shoes. Everything about this photo screams I! AM! A! MOVIE! STAR!

gown, dress, clothing, hair, wedding dress, shoulder, bridal party dress, blond, fashion model, formal wear,
gown, dress, clothing, hair, wedding dress, shoulder, bridal party dress, blond, fashion model, formal wear,

Renée Zellweger

The Year: 2004

The Win: Best Supporting Actress, Cold Mountain

The Dress: Hello and welcome to Renée Zellweger's bow, courtesy of Carolina Herrera. According to the designer, "She had just finished the second Bridget Jones movie, so I took advantage of her being a little curvier than usual. Thankfully Renée loves fittings, because nothing matters more than a perfect fit, especially with a strapless... I copied the bow in my bridal line and it was one of the best-selling wedding gowns I've ever done."

Red carpet, Carpet, Gown, Dress, Flooring, Clothing, Shoulder, Hairstyle, Fashion, Premiere,
Getty Images

Cate Blanchett

The Year: 2005

The Win: Best Supporting Actress, The Aviator

The Gown: Yellow is always a refreshing color to see on the red carpet, and this Valentino gown—paired with that red lip!—killed it.

hair, clothing, white, dress, yellow, shoulder, gown, blond, formal wear, beauty,
hair, clothing, white, dress, yellow, shoulder, gown, blond, formal wear, beauty,

Reese Witherspoon

The Year: 2006

The Win: Best Actress, Walk the Line

The Look: There's a reason Reese's gown looks so classic and timeless. It's vintage Dior from 1955, and is, frankly, what fashion dreams are made of.

Performance, Fashion, Event, Talent show, Award, Singer, Performing arts, Fashion design, Singing, Music artist,
Getty Images

Rachel Weisz

The Year: 2006

The Win: Best Supporting Actress, The Constant Gardener

The Look: Rachel was seven months pregnant when she won her Oscar, and turned to designer Narciso Rodriguez to create the perfect gown to accessorize her bump in what she called a "surreal"moment on the carpet.

Red carpet, Carpet, Dress, Flooring, Clothing, Gown, Shoulder, Hairstyle, Fashion, Fashion model,
Getty Images

Jennifer Hudson

The Year: 2007

The Win: Best Supporting Actress, Dreamgirls

The Look: Very into the fact that Jennifer Hudson dressed to complement the Oscar she clearly knew she was about to win. Props to Oscar de la Renta for this genius.

79th Annual Academy Awards - Show
Kevin Winter - Getty Images

Marion Cotillard

The Year: 2008

The Win: Best Actress, La Vie en Rose

The Look: Forever screaming at how perfect this mermaid dress—with literal fabric scales!—is on Marion. According to designer Jean Paul Gaultier, she "initially requested something simple, but I wanted everyone to see the woman I saw."

Gown, Red carpet, Carpet, Dress, Flooring, Clothing, Fashion model, Fashion, Premiere, Shoulder,
Getty Images

Penélope Cruz

The Year: 2009

The Win: Best Supporting Actress, Vicky Cristina Barcelona

The Look: Penélope pulled a Reese Witherspoon and wore a vintage Balmain ballgown from 1950. As Tim Gunn noted, “It’s really a museum piece.”

Gown, Dress, Red carpet, Carpet, Clothing, Fashion model, Wedding dress, Flooring, Bridal party dress, Bridal clothing,
Getty Images

Kate Winslet

The Year: 2009

The Win: Best Actress, The Reader

The Look: Kate paired her Atelier Yves Saint Laurent by Stefano Pilati dress with Grace Kelly's signature hair, and honestly, yes please.

kate winslet
Dan MacMedan

Mo'Nique: 2010

The Year: 2010

The Win: Best Supporting Actress, Precious

The Look: Loving this regal blue color on Mo'Nique, who was dressed by Tadashi Shoji. She paired the gown with white gardenias in honor of Hattie McDaniel, the first African-American actress to win an Oscar.

Cobalt blue, Yellow, Red carpet, Blue, Dress, Shoulder, Carpet, Electric blue, Flooring, Fashion,
Getty Images

Sandra Bullock

The Year: 2010

The Win: Best Actress, The Blind Side

The Look: I'd describe this one as "Disco ball but make it a Marchesa Oscar gown."

Yellow, Dress, Clothing, Gown, Fashion, Shoulder, Fashion model, Haute couture, Hairstyle, Statue,
Getty Images

Natalie Portman

The Year: 2011

The Win: Best Actress, Black Swan

The Designer: Natalie Portman worked with Rodarte on her Oscars dress, which makes perfect sense—the designer sisters created the costumes for Black Swan, including Natalie's stunning feather-y tutu.

Yellow, Dress, Shoulder, Formal wear, Fashion, Event, Gown, Temple, Floristry, Flower,
Getty Images

Octavia Spencer

The Year: 2012

The Win: Best Supporting Actress, The Help

The Dress: Like Charlize, this is just one of those dresses (by Tadashi Shoji, FYI) that just screams I AM RED CARPET ROYALTY. Also shoutout to whatever that lady in the background is doing with her legs here.

84th Annual Academy Awards - Arrivals
Steve Granitz - Getty Images

Anne Hathaway

The Year: 2013

The Win: Best Supporting Actress, Les Misérables

The Look: This dress caused so. much. drama. Basically, Anne was supposed to wear a Valentino gown to the Oscars, and the brand released a statement claiming as much before she walked the carpet. But then Anne showed up in Prada because she heard another actress was wearing a similar look, so she ended up having to issue a public apology. Hate when that happens.

Dress, Yellow, Statue, Gown, Shoulder, Sculpture, Figurine, Formal wear, Wedding ceremony supply, Temple,
Getty Images

Jennifer Lawrence

The Year: 2013

The Win: Best Actress, Silver Linings Playbook

The Dress: Dior, naturally. AKA the gown J.Law tripped and fell up the stairs in.

Gown, Fashion model, Dress, Clothing, Red carpet, Carpet, Wedding dress, Flooring, Shoulder, Bridal party dress,
Getty Images

Lupita Nyong'o

The Year: 2014

The Win: Best Supporting Actress, 12 Years a Slave

The Look: Lupita chose the color of this Prada dress because "it's a blue that reminds me of Nairobi, so I wanted to have a little bit of home." She paired the gown with a Fred Leighton headband and it was *chef's kiss* perfection.

Red carpet, Dress, Carpet, Flooring, Gown, Premiere, Event, Shoulder, Fashion, Haute couture,
Getty Images

Alicia Vikander

The Year: 2016

The Win: Best Supporting Actress, The Danish Girl

The Look: Another glorious buttercup yellow moment on the red carpet, this time courtesy of Louis Vuitton and a whole lotta sparkles.

Dress, Clothing, Gown, Carpet, Yellow, Red carpet, Strapless dress, Fashion, Fashion model, Flooring,
Getty Images

Brie Larson

The Year: 2016

The Win: Best Actress, Room

The Look: Gucci + Ruffles + a big belt = Oscar dress perfection.

Gown, Dress, Cobalt blue, Clothing, Fashion, Haute couture, Fashion model, Fashion show, Formal wear, Event,
Getty Images

Emma Stone

The Year: 2017

The Win: Best Actress, La La Land

The Dress: Emma looked like Old Hollywood royalty in this Givenchy Haute Couture dress by Riccardo Tisci, which was gorgeously fringed and made everyone immediately want to become a flapper.

Red carpet, Dress, Carpet, Gown, Clothing, Flooring, Fashion model, Fashion, Shoulder, Hairstyle,
Getty Images

Viola Davis

The Year: 2017

The Win: Best Supporting Actress, Fences

The Look: How to make a statement on the red carpet. Step One: Wear a hot red dress by Armani Privé. Step Two: Be Viola Davis.

Figurine, Standing, Flooring, Carpet, Statue, Sculpture, Muscle, Toy, Red carpet, Art,
Getty Images

Regina King

The Year: 2019

The Win: Best Supporting Actress, If Beale Street Could Talk

The Look: Regina King sees Angelina Jolie's famous Oscars leg slit, and would like to raise it approximately 4 inches with the help of Oscar de la Renta.

Fashion model, Clothing, Dress, Beauty, Leg, Fashion, Cocktail dress, Thigh, Hairstyle, Human leg,
Getty Images

Ruth E. Carter

The Year: 2019

The Win: Best Costume Design, Black Panther

The Look: Ruth's blue, metallic gown and beaded necklace absolutely popped at the 2019 ceremony. The veteran designer has been behind the looks from so many fantastic movies, so this Oscar gold was long overdue.

hollywood, california february 24 best costume design winner for black panther ruth e carter poses in the press room at the 91st annual academy awards at the dolby theatre in hollywood, california on february 24, 2019 photo credit should read john rasimusfuture publishing via getty images
Future Publishing - Getty Images

Laura Dern

The Year: 2020

The Win: Best Supporting Actress, Marriage Story

The Look: We all know that the Supporting categories usually steal the whole show. Laura earned her first Oscar as family lawyer Nora Fanshaw, and arrived at the ceremony in a pink custom Armani Privé gown, embellished with gorgeous black tassels, embroiderey, and crystals.

hollywood, california february 09 laura dern poses at the 92nd annual academy awards at hollywood and highland on february 09, 2020 in hollywood, california photo by steve granitzwireimage
Steve Granitz - Getty Images

Chloé Zhao

The Year: 2021

The Win: Best Director/Best Picture, Nomadland

The Look: Wearing a nude Hermés dress paired with crisp white sneakers, Chloé is glowing at the 93rd Academy Awards, where her film Nomadland was the big winner of the night.

chloé zhao, winner of the best director for 'nomadland,'
Handout - Getty Images
emerald fennell, winner of best original screenplay for
Handout
yuh jung youn, winner of best actress in a supporting role for
Handout
jessica chastain, winner of best actress in a leading role award for the eyes of tammy fay
Future Publishing
2022 ariana debose accepts the award for best actress in a supporting role for her performance in west side story
Myung Chun
2022 billie eilish arrives on the red carpet outside the dolby theater for the 94th academy awards in los angeles
Future Publishing
michelle yeoh, winner of the best actress in a leading role award for everything everywhere all at once, attends the 95th annual academy awards governors ball at dolby theatre
Emma McIntyre

Jamie Lee Curtis

The Year: 2023

The Win: Best Supporting Actress, Everything Everywhere All at Once

The Look: Wow, what a silhouette! Jamie's crystal-covered Dolce & Gabbana gown was timelessly glamorous.

jamie lee curtis, winner of best actress in a supporting role award for everything everywhere all at once
Rodin Eckenroth

Da’Vine Joy Randolph

The Year: 2024

The Win: Best Supporting Actress, The Holdovers

The Look: Da’Vine Joy won her much-deserved Oscar in a pale blue custom Louis Vuitton gown with gorgeous puffy sleeves and a long train. It was the first Oscars she has attended, and likely won’t be the last.

davine joy randolph, winner of the best supporting actress award for the holdovers
Dania Maxwell

Robert Downey Jr.

The Year: 2024

The Win: Best Supporting Actor, Oppenheimer

The Look: Robert was one of the best-dressed male stars of the night by a country mile with his black Saint Laurent suit, paired with a unique bolo tie, and great wide-legged high-waisted trousers.

robert downey jr, winner of the best actor in a supporting role award for oppenheimer
Jeff Kravitz

Justine Triet

The Year: 2024

The Win: Best Original Screenplay, Anatomy of a Fall

The Look: Justine, who won the Best Screenplay award for the excellent legal thriller she wrote with her partner and co-writer Arthur Harari, wore a chic embroidered custom Louis Vuitton suit over a satin top.

arthur harari and justine triet winner in the category best original screenplay for anatomy of a fall
Dania Maxwell
christopher nolan and emma thomas attend the 96th annual academy awards on march 10, 2024 in hollywood, california
Mike Coppola
holly waddington, winner of the best costume design award for poor things poses in the press room during the 96th annual academy awards at ovation hollywood on march 10, 2024 in hollywood, california
Jeff Kravitz

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