I have never, in my entire life, seen Leandra get starstruck. She remained cool as a cucumber around Gwyneth Paltrow. But something about Drew Barrymore hit a nostalgic nerve somewhere in the back of Leandra’s subconscious where she realized — and then had a hard time forgetting — the she was in the presence not only of a beloved American actress who has a successful beauty line, Flower, but sitting next to the one and only Josie Grossie.

Or as Garry Marshall-as-her-Chicago Sun-Times boss called her, “José.”

Enjoy as Leandra and Drew Barrymore talk about Flower, contouring, avoiding the “pitfalls of Hollywood” and, yes, Josie Grossie.

Watch Charlotte Tilbury make Leandra look like Penélope Cruz (ish).

Photographed by Simon Chetrit; follow him on Instagram @simonzchetrit.

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  • Mary

    I loved this, such thoughtful conversation but the editing made it feel so incomplete and spliced! I want to see and hear more of this exchange because the small clips of advice really resonated

    • Leandra Medine

      oooo, we gonna turn the full convo into a podcast episode! just kind of challenging to have such a long convo appear in video form, but this is great feedback thanks mary love ur name

      • Mary

        Soo happy to hear, I thought her story about changing her life in a drastic way instead of “sleep on it/exercise/etc!” was awesome and refreshing, plus she’s cool and real. Like you. Thanks ily your name and outfit!

      • JB

        Oh my god. THANK GOD. I didn’t want this conversation to end and was hoping for this good news in the comments. Can’t wait for the full pod.

  • Jessica

    About 10 years ago, I lived in LA and worked at a talent agency, specifically, the agency that repped Drew. I’d see her in our offices every once in a while, and she was one of the few celebs that really made me swoon.

    More importantly, my boyfriend at the time lived on the same block as her boyfriend at the time, who was none other than Fabrizio Moretti (sp??) of The Strokes. Not even exaggerating — occasionally they’d sit outside his house on the curb at dusk while he strummed the guitar. I’d literally sit by the window and watch them.

    Yes, stalker… I love her so much.

    Edited as I momentarily forgot it’s been 10 damn years since 2007.. oh my

  • Coco

    yes yes yes love you Drew and Leandra.

  • hi drew… what is on your eye lids? is it your line? i want to buy it in the next 3 minutes. thanks! i could have watched 50 more minutes of this interview.

    • Leandra Medine

      its from her line11!!@!@

      • is it one of those sticks?

        • Leandra Medine

          I think so but also don’t want to put words in her mouth so here’s hoping she replies!

          • here’s hoping she doesn’t reply directly to me because i would faint and be hospitalized.

  • Hellbetty666

    a) this was wonderful. Can we have a weekly session of Drew and Leandra’s life lessons?
    b) Leandra, your eyebrows are making me weep, they are so beautiful, man I’m jealous. Also I love your voice (not your singing voice) sorry if this is borderline inappropriate!
    c) I can’t wait to hear the whole thing
    d) so about that weekly show….
    e) legit cackled at Drew’s “that’s not classy” comment!

  • Olivia AP

    I loved this conversation.
    And Drew seemed wise

  • Andie

    You brave and amazing women!!! My heart just exploded ❤❤❤❤❤ never been kissed was such a big movie for me and my sister. In my family we still say you’re not Josie grossy anymore!

  • JB

    Dearest Drew,
    Can we be BFFs?


  • KK

    So relatable. My resolution was to make this a Year of No and it is so EMPOWERING. Plz write this book Drew so I can write the foreword.

  • kjrobot

    Why do I love Drew Barrymore SO much?!?! Who cares. I just do! She’s sweet and honest about growth and has her own opinions and speaks them without judging others. Thanks for this interview MR team!

  • Bree


  • Didi Beck

    Wowowow, LOVE this. Especially the opening segment on stress. There’s so much “advice” floating around the internet and irl about taking deep breaths and sleeping more and exercising and Beyonce having the same amount of hours in a day that everyone else does but none of it helps, ever. It’s refreshing to see two kickass women talk about this and how it totally doesn’t translate to real life.

    Leandra– thank you thank you thank you for always remaining true to your ethos and looking like a real human being on camera, sans hairspray and foundation and lash extensions and fillers. It’s easy to forget sometimes that the Kendalls of the world aren’t the standard for “normal.” Your attitude toward personal style seriously helps me well beyond the scope of fashion.

  • Parinaz Shahmoradi

    The set (furniture, colors in the background, …) in which you film the chatroom videos in, I love them. One of the things that makes these videos different and cool.

  • Christina

    Never been kissed is one of my all-time favorite movies. Actually when I first watched it I had literally “never been kissed” (the only one amongst my friends) and it struck a chord with me. Also, I loved how honest both Drew and Leandra were about dealing with some difficult personal issues and leading “imperfect” lives.