Alexis Oakley on glamming Kris Jenner and what we took from Justin Bieber… - Ep. 21

Brand Safe

Tana Mongeau interviews celebrity makeup artist Alexis Oakley about their decade-long friendship, tracing its origins from a chaotic basement glam session to a

Key takeaways

• Alexis Oakley began assisting Ash Kholle after two years of relentless outreach, landing her first major day on Ariana Grande's "God is a Woman" music video shoot.
• Working with Kris Jenner was a career-defining moment for Alexis, who describes the reality star as incredibly polite and professional despite initial nerves.

Main topics

• Friendship origins and loyalty
• Celebrity makeup artistry career path

Notable quotes

"If you want to be a celebrity makeup artist, you will not have a life outside of them. Their life is your life."

Conclusion

The episode offers an intimate look at the evolution of a high-profile

Transcript preview

Speaker 1 (0:00) Alexis Oakley, the woman, the myth, the icon, the celebrity makeup artist, the influencer, and most importantly, my best friend and favorite person. Oh my god, I love you. We are so brand safe. So brand safe. Speaker 1 (0:17) I have been dreaming of this for so long. Me too. Are Speaker 2 (0:21) you Speaker 1 (0:21) kidding? I Speaker 2 (0:21) cannot Speaker 1 (0:21) thank you enough. Let me take my sunglasses off. It's like you're indoors. Oh my God. Don't thank me. Thank you. Are you kidding? Thank you for giving me a career. Thank you for letting me sit in this chair. You're so, she always says that to me. And I think it's so sweet. It attests to your character. But everything you have is so deeply because of who you are. You are one of the most hardworking, inspiring, creative, talented, like. patient. I could go on for days. My love for you. Like just individuals that I know. And I'm so inspired by you. And I swear when I started this show, when I was telling people like who I wanted to interview, you were always in my top five because it's just like, I want to interview you. You have so much to say. You've done so much in your lifetime. And I'm so excited to talk Speaker 2 (1:00) about it. I'm so excited. We're a little nervous. Speaker 1 (1:02) We were being nervous before we started filming just because like we've never really had a moment like this. No, Speaker 2 (1:07) I mean, you've been on like my YouTube channel and different things before, but this just like feels so serious. It does. And like I've Speaker 1 (1:12) a blazer on but it's you you make me want to have good posture and a blazer on I don't know what it is it's just who you are you're so like together as a person you and I have also been through so much and so many eras together it's Speaker 2 (1:24) actually scary Speaker 1 (1:24) and I kind of I have so many questions today about your work ethic about your celebrity clients about your dating life like all these things but I kind of want to bring it back to the beginning to the first time that we met And something that's really funny about yours and I's relationship, obviously, is that you were beautifully glamming and putting together an alcoholic for so many years, right? Like you were like beauty blending away the bad decisions that I'd made. So you always will like piece together memories for me. That is type B and type A. Well, do you even remember the first time we ever glammed? I was thinking about this earlier. I think I do. But tell me, tell me, and then I'll tell you. Speaker 2 (2:00) It was at your house in the basement. And it's funny Speaker 1 (2:04) because the basement was just my bedroom. Yeah. Speaker 2 (2:06) Yeah. Speaker 1 (2:06) But it was the desk outside Speaker 2 (2:08) of Speaker 1 (2:08) your Speaker 2 (2:08) bedroom. You were going to a girls night, I think, for MTV. You were shooting the show. And I remember I was having a really hard time doing your makeup. I'm not going to lie, because you were moving a lot. And you were the first client that I had ever had that I had to learn to kind of work around that. And so I never told you this at the time, but the wing just kept getting thicker and thicker and thicker. And Speaker 1 (2:27) I Speaker 2 (2:27) loved it. I was like, make me Amy Winehouse. I want my wing to touch the ceiling. I was trying to pretend as if that was the look. And that's what we were going for, even though it wasn't at all. But you loved the glam. And the next day, you were like, can you come back again tomorrow? So I was like, okay, I guess I did something Speaker 1 (2:39) right. You did everything right. Do you want to know what I remember from that moment? That's like so random is that we were listening to Avril Lavigne. Were we? I don't even remember that. And Speaker 2 (2:47) then life just went Speaker 1 (2:47) on. And so many things happened in like that realm and stuff. That's all I remember. That's Speaker 2 (2:52) so funny. I do remember too, Natalie being there because Natalie was your assistant at the time. And I remember she pulled me to the side at one point and she was like, I just want you to know Tana thinks this is a really big deal. Like she considers you a Mario. Like this Speaker 1 (3:03) means the world to her. I was like, what are you talking about? Which I did. I was so excited to glam with you and like all of the things that you had done and stuff. And I never thought in that moment that our relationship would become this. And now I'm like so loyal to you. Like if you can't do my makeup because you're in Venice or doing whatever, it's like I'm doing my own beat. Like it is you and me for the rest of life, you know? And that Speaker 2 (3:22) means so much because I feel like that's so rare as a makeup artist. I feel like it's really common for people to kind of like makeup artist hop and that's just kind of the norm. Yeah. You are the most loyal client ever. Speaker 1 (3:33) But it's because A, you're so f***ed. Even on my worst day, I remember we had an era where I had periorbital cellulitis. My eye would swell up the size of a golf ball and you would come over and you would contour my eye before I would go on the morning news. I was going on KTLA and like all those different things. You have this way of making me feel like everything is and it's a vape on the floor. But you have this way of making me feel like everything is going to be okay. It's also a personal thing, you know, like the therapy sessions in the chair and all the different things. It's just you and me forever. The second part of it is also like your patience. Like You are so patient when it comes to the way that I am in the chair. But Speaker 2 (4:08) I love you so much, like genuinely. And people ask sometimes, like, how do you like, you know, you're a very like on time person. Like, Speaker 1 (4:14) how do you deal with it? But honestly, I love you so much. No, Speaker 2 (4:17) I really do love you so much. And I appreciate everything you've given me. And I know you always say like, no, it's not true. But I really want to have a career if it weren't for you. And I would literally clean the bottom of your feet if you asked me to. I would do anything for you. You have glammed my p***y. I have. And you have Speaker 1 (4:32) glammed my nips a couple times. Yeah. But other than that, I think that's as far as it'll go. I'll clean the bottom of my own feet. I don't wish that on my worst enemy. Do you remember when Speaker 2 (4:40) we scrubbed your ankles with the magic eraser? Speaker 1 (4:43) No. Speaker 2 (4:43) Please tell me about that. I remember. I think it was Halloween week because we were just like tanning and glamming and tanning and glamming. The spray tan was building up real bad. And this was before the chemical burn of it all situation. But I remember we like tried it out and it worked. We magic erased my ankles for what look? I don't even remember. I just remember it was Halloween week and your tan was like looking a little scary. So we like. Speaker 1 (5:05) And you're always really good about that too. Like I'll walk out. Even right now I kind of have like a bodybuilder tan where like my body is so much darker than my face and I should be doing the like sideways pose and I'm really scared of it. And you're always gonna push me to like get in the shower and scrub it off. You're like Tanya you can't leave the house like that. begging and then I'll fight you on it and you'll be like get in the shower we've Speaker 2 (5:23) had Speaker 1 (5:23) a lot of fights over showering Speaker 2 (5:26) Which is not Speaker 1 (5:27) good. It's Speaker 2 (5:28) not Speaker 1 (5:28) good. I'm like proud of this era, obviously. I'm like grateful for it. But all of the past eras are so crazy. I mean, it's so funny looking back to the way I would be like, I'm going to Starbucks today and I'm going to get paparazzi with Harry Jowsey. Can you glam me? It's like, girl, you don't need a glam for that. But Speaker 2 (5:42) you do. Speaker 1 (5:42) And that's how I paid my rent. So thank you for that. It is like there's no better feeling in the world than like leaving with a good glam. Oh my God, it's the best. Can I tell you something right now? I need a Speaker 2 (5:54) Zofran. I Speaker 1 (5:54) shot up yesterday. Speaker 2 (5:55) I Speaker 1 (5:55) shot up yesterday and it's fierce. She's back. Correct me if I'm wrong, but was I one of your first like solo clients? Speaker 2 (6:01) Yeah, you were. Speaker 1 (6:02) Yeah. Speaker 2 (6:02) I was working with Lisa Rinna, Paris Hilton, Avril Lavigne. Speaker 1 (6:07) No wonder I was so gagged at the time. I was like the Paris of it all. I remember is what did it for you. I Speaker 2 (6:12) think you might know this, but maybe we haven't talked about this online before, but you were like a dream client of mine. You were on like my dream client list for a really long time. You raised me. Obsessed. I love Speaker 1 (6:22) you. Speaker 2 (6:22) And I remember I saw you at Chop Stop one night. I was there with my friend. And that's the first time I had ever seen you in person. I was like, oh my god. Like, I have to go up to her. But then I'm like, I don't have business cards. Like, she's not going to take down my number or my Instagram right now. I Speaker 1 (6:34) so Speaker 2 (6:34) would have. Speaker 1 (6:34) I used to be hammered at that Chop Stop all the time. The one on Ventura. Amazing. That's Speaker 2 (6:38) the Speaker 1 (6:38) one. The Sherman Oaks one by the Tender Greens. Speaker 2 (6:41) That's the one. And so I was like, what do I do? And that night I went home and ordered business cards. I didn't go up to you because I was like, this just isn't going to be what I like want it to be. And then like two weeks later, we were at an Austin Mahomes Valentine's Day party. We were at that. What's the place with the trap door? No Speaker 1 (6:56) vacancy. And Speaker 2 (6:57) someone introduced us. And as soon as she said that I work with Paris, you were like, give me your Instagram. Speaker 1 (7:04) And then we started glamming. Yeah, but it took like a year and a half. And that's something that you've always been so incredibly patient. And like when it comes to manifesting your dreams. So I don't know why I was one of them, but like I digress. Hey, it changed my life. No, I love you. I want to go all the way back to the brides at your house in your basement because I think it speaks and it like it just attests so much to who you are. And then I want to move to Ash K home and then I want to. Speaker 2 (7:26) Yeah. Yeah. So I started off doing brides and prom girls in my parents basement. They would bring over their own foundation because I didn't have. many shades and it was $40. Don't you wish you got it at that? Oh my Speaker 1 (7:37) God. No, you're worth so much more than that. Truly. But yeah, I mean, I Speaker 2 (7:41) only ever did a few brides. I feel like it was primarily prom girls, but I did that for a few months and then immediately moved to LA because I moved to LA right after high school. And Speaker 1 (7:50) you just knew? Knew. What was going through your head in that move? I always find it so interesting because obviously choosing to move to LA is just like packing up all your. and going based on self-belief and it's scary as f**k. Like what did that, what did those first few months look like for you? The Speaker 2 (8:03) first few months I was in makeup school. So the whole reason of me moving out was I'm going to go to makeup school. It's five months and if I hate it, I'll move back to Missouri. If I love it, I'll end up staying. Honestly, I had no fear and I think it's because I was so young. All my friends were going off to college and stuff. So to me, it felt like the same thing. But I really had no fear. I was just like, I know this is going to work. I know it's going to happen. But I don't know if Speaker 1 (8:23) I Speaker 2 (8:23) would be that same way now. But I think when you're Speaker 1 (8:25) young, you're so unstoppable. I've been in a serious era of yearning for that. Like yearning for that. Just like nothing has scathed you and you believe the self-belief. But delusional like, or, you know, confidence and all those things. really can get you to like where you need to go. Yeah. Speaker 2 (8:38) What Speaker 1 (8:39) is your biggest advice for someone who like wants to follow their dream, move out of their state, like go big or go home? I Speaker 2 (8:44) think if you feel like you can do it, you just have to go for it. But you also have to be prepared for rejection. I always say I heard more no's than yeses in my entire career. And I never once let that get me down or let me feel like I wasn't good enough or I couldn't make it. I feel like it just always was like a redirection for me. And that's always how I viewed it. And I think that's so Speaker 1 (9:02) important for people because you're going to hear no. That ended up making. you hear a lot of yeses as well. You just never gave up. It's such good advice. And so speaking of, you know, hearing the no's to get to the yeses, obviously you started with the brides, which I always think is so cute because do you like doing wedding makeup? Not at all. Yeah. You just Speaker 2 (9:18) did Tara's world of wedding makeup and Speaker 1 (9:20) you slayed it. Thank you. Yeah. But Speaker 2 (9:22) no. Speaker 1 (9:23) Is it just because it's the same thing and it's like the pressure? Speaker 2 (9:25) Well, honestly, I always say working with brides is so much harder than working with celebrities. And I feel like people want it. think that's the case but with a wedding that person's getting their makeup done most likely for the first time ever in their life maybe a few random times or a prom or something like that so the pressure that they go into like is no joke for the wedding they want to look the most perfect they've ever looked but they want to look like themselves but they're not used to heavy makeup but you have to have heavy makeup in order for it to photograph right so i feel like it's just never a good experience but with celebrities they get their makeup done every day so they're so used to seeing themselves like that yeah Speaker 1 (9:58) oh my god i feel like i would go home and cry after doing a bride it's because the pressure is just so so on yeah you were always meant to be a celebrity makeup artist which brings me to the ashk home of it all so before you started doing makeup on your own you were assisting the iconic the legendary ashk home she does the kardashian so many people how did you transition into Speaker 2 (10:20) that? So I knew that if I wanted to stay in LA after makeup school, I had to find a job. My parents were definitely willing to support me financially, but I had to show that there was like a reason for me to be here. Speaker 1 (10:29) So Speaker 2 (10:29) while I was in makeup school, I harassed everyone, every makeup artist begging, begging, begging to get someone to hire me. And I first started working with Rachel Goodwin, who does makeup for like Emma Stone and more of like the actresses, like A-list actresses. And I did that for a while. And I absolutely loved working with her too. But I, Kardashians was like my end goal. that's my kind of glam yeah it's like Speaker 1 (10:49) full b i Speaker 2 (10:50) was reaching out to ash for two years before i ever had the opportunity to work with her and she was and what did Speaker 1 (10:55) that look like just emails emails emails Speaker 2 (10:57) copy paste copy paste literally just please let me assist you i'll work for free i promise i'll assist you once and like your life will change i'll be the best assistant i'll do this for you i'll do this for you like really hyping myself up i would see her at events i would beg her in person like it was just i mean what did in person look like same thing same thing i'm just like ash like i love you so much Please let me work for you. And she's like, I really appreciate it. But like, I don't use assistants. Like, I do it on my own. But like, thanks so much. She was always really, really kind and definitely like gave me enough that to make me keep trying, I guess, obviously. And then finally, one day she posted that she was hiring. So I reached out again. We did an interview. And the first time I ever worked with her, actually, first time I ever really even like had a long conversation with her was Ariana Grande's God is a Woman music video. That was my day one with her. The Speaker 1 (11:43) goosebumps. Speaker 2 (11:44) Insane. Speaker 1 (11:45) And that was the purple look. Yes. Right? Yeah. And she was doing that. Yeah. And she needed you to assist on that. That is, again, that speaks so much to who you are. I would show up and shit myself. Like, genuinely, what do you mean? And that glam is so legendary. No, it was insane. Speaker 2 (12:00) Such a fun era. What did that day look like? It was just a really long day on set. Like, music videos are usually two days. So it was like a two-day shoot. And honestly... I just help carry her brushes. I help clean things for her. I help organize things for her. Like assisting really isn't glamorous. Yes, you get to be in incredible rooms, but I was very behind the scenes, very much seen, not heard, one of those types of situations. What's your best Speaker 1 (12:22) advice for that as well? Because obviously you're assisting with an end goal. That's kind of like a stepping stone for you to be the Ashkay home in this situation. You know what I mean? And it's a lot of dirtier work and being quiet and like all of those things. What is your advice and outlook? on that time? I think reading a Speaker 2 (12:37) room is so important. I think if you want to work with celebrities, period, reading a room is really, really important. But especially when you're assisting, you are truly there to be a fly on a wall and seen but not heard. And one of the biggest compliments you can get as an assistant is you're so quiet. You're so polite, like things like that. And I feel like I was always really good at reading a room. So like if something was maybe happening where a client was. really opening about something and it felt like a therapy session, I would just step out of the room and text Ash and be like, hey, I'm standing right outside the door. Text me if you need anything. Speaker 1 (13:06) God, the tea though. I Speaker 2 (13:07) know. The self-restraint. Speaker 1 (13:09) I know. A-list celebrity spilling. You're like, I'll be in the hallway clenching. Speaker 2 (13:13) But that is like what gets you called back, I think. And I think Ash really appreciated that and saw. that I wasn't there just to post on Instagram that I was her assistant. Obviously, she allowed me to, which was really nice because that's not always the case. But I think just like being a helping hand is so important and being humble too because I think a lot of people just want to move over the assisting period and it taught me so, so, so much. Speaker 1 (13:36) Yeah. I feel like almost shadowing her and like all of the things that she was doing was able to like help you build. the building blocks, I guess, the first level of becoming a celebrity makeup artist yourself. For sure. And Ash truly is like the Speaker 2 (13:47) most professional person I've ever worked with. The way she interacts with her clients, the way she is as an artist, everything about her, I really admire. And I knew I wanted to be like a copy and paste of her Speaker 1 (13:57) essentially. And so I learned so much working with her. Who was your favorite person to assist on with Ash? Speaker 2 (14:03) I mean, honestly, all of them were so fucking iconic. Like during that period, I had the opportunity to assist her with Ariana Grande's makeup, Kim Kardashian, Khloe. I mean, the Kardashians were so iconic, obviously. I feel like Speaker 1 (14:16) either Speaker 2 (14:16) Kim or Speaker 1 (14:17) Ariana. Did you ever feel like you also learned something maybe from the celebrity that you were assisting on? Speaker 2 (14:22) Yeah, definitely. I mean, I think the Kardashians are truly like the most professional people in the world as much as people like to shit on them. They always showed up on time. Which Speaker 1 (14:30) we don't do Speaker 2 (14:30) over Speaker 1 (14:31) here. Speaker 2 (14:31) Oh my God, never. They always Speaker 1 (14:32) showed up on time, mogging Speaker 2 (14:34) me. But like, they truly are so professional. And they're at the place, obviously, they don't have Speaker 1 (14:40) to be. They're a dream client to work with, truly. What is Kim Kardashian like across the glam? Speaker 2 (14:44) Most of the time, when you're working with someone of that caliber, it's not like a kiki, like people expect. They're very kind. They're very nice. But... It's not like we're like sitting talking the whole time. They're very much just like in work mode doing their thing. And to them also, and I feel like you've been through phases of this too, but it is such a daily part of their life to where it's not necessarily like this exciting thing. Like we're getting clean. Yes. It's just like them doing their own makeup. It's like, oh, again. Yeah. Like just another task in the day. Yes. Speaker 1 (15:14) crazy. And so how long was the Ash K. Holm period before you started moving into the Alexis Oakley period? That Speaker 2 (15:20) was probably for about a year and a half. She was the last person that I assisted. And so it was definitely a little faster, my period with her. And the only reason why I left, I probably still would be her assistant, honestly. But the only reason why I left was because I got the opportunity to go on tour with Avril Lavigne. And I couldn't do both, obviously. And Ash was so nice when it came to me leaving her and everything, which is really great because I feel like that's not always the case, too, when you leave an artist. Yeah. Speaker 1 (15:44) Did you ever miss it? Like because obviously you're choosing to like jump into a water and just trust yourself and it's not this consistent pay and you're leaving like the Chloe's and the Kim's and the Ariana's and trying to like you know do your thing. Speaker 2 (15:54) Yeah. Was it scary? So scary. So scary because for the longest time I was not making enough money financially to just do clients on my own and I truly needed that assistant job to pay my bills but it was really scary and honestly I went back to assisting during COVID. Yeah. I'd taken time off for probably like a year and a half and then I became her assistant again during COVID just because Speaker 1 (16:14) I like needed the money. Did you feel different that next time that you'd learned so much? It was hard. I'm not going to Speaker 2 (16:19) lie because I would be in the room feeling like I should be in this room on my own, not assisting. So it was definitely hard. And I think that's when I knew like I really got to close this chapter because I'm not walking in any more excited to learn something. I feel like. Speaker 1 (16:33) I've learned it. Speaker 2 (16:34) Yeah. And I do think you can always continue to learn, obviously. But I didn't have the right attitude to be an assistant at that point, Speaker 1 (16:40) I don't think. But that's so cool. You'd established yourself as a celebrity makeup artist. Yeah. And you were doing your big one. And I can't believe it really is just so crazy looking back at like our beginning era, like the things that you had to deal with with me, even you talking about like Kim's environment and stuff being like not a kiki and just kind of like everyone's super professional, like the things that you have seen in my house. And the things that you've like, I feel like I've