Design Matters 20th Anniversary Celebration

Featuring: Brian Rea, Maira Kalman, Barry Blitt, Edel Rodriguez, Christoph Niemann
Host: Debbie Millman
Date: November 3, 2025

Episode Overview

This special episode of Design Matters celebrates two decades of the podcast by bringing together memorable conversations with five of the most visionary contemporary illustrators: Brian Rea, Maira Kalman, Barry Blitt, Edel Rodriguez, and Christoph Niemann. Through a montage of past interviews, host Debbie Millman explores each artist’s creative arc, their philosophies on illustration, and the experiences that have shaped their careers. The episode encapsulates the soul of visual storytelling, offering rare insight into the world of editorial and conceptual illustration.

Key Discussion Points & Insights

1. Brian Rea: The Journey from Baltimore to The New York Times

• Evolution of Style and Storytelling
  • Early work was collage-driven; later shifted to drawing from life, capturing real stories and authenticity ([04:57]).

    "The drawings that were telling stories that were feeling more real... not so style driven." —Brian Rea (05:19)

• Breaking into the Industry
  • Rejected repeatedly when first visiting New York post-graduation; persistence led to eventual success ([07:10]).

    "I remember walking in and the woman said, 'Didn't I tell you to put it in the mail?' I said, 'Yeah, but today the mail's coming in person.'" —Brian Rea (00:01 & 07:36)

• Getting the Op-Ed Art Director Role
  • Landed the job in part by bluffing ("I lied"), then proving himself in various sections.

    "I just said... if you give me maybe three days of training... if it doesn't work out... you can get rid of me." —Brian Rea (10:01)

• Working at Pace
  • The Op-Ed section requires fast turnaround, reaching out to admired artists, managing burnout, and relishing moments when illustration energizes public discourse ([12:25-14:02]).

    "Once you lock into it, it's almost like you have an internal time clock... it's also exhilarating, too." —Brian Rea (12:25)

2. Maira Kalman: Embracing Mystery, Spontaneity, and Canine Muses

• Fluid Identity and Centering
  • Kalman reflects on not always knowing who she is, embracing the mysteries in life ([14:26]).

    "How do you know who you are? Half the time I do not know who I am. There is not one static place. How do you stay so centered?" —Debbie Millman (14:26) "Well, that's a mystery." —Maira Kalman (15:01)

• Lincoln as Humanist
  • Describes Abraham Lincoln’s extraordinary blend of kindness and intelligence ([15:25]).

    "He had the great love of humanity, which is really something that shines through all of these decades." —Maira Kalman (15:25)

• Dogs as Inspiration & Companions
  • Early caution about dogs shifted after her family got Pete, leading to an ongoing creative obsession ([16:33-18:29]).

    "The most important decisions are made without any thought at all." —Maira Kalman (17:05) "They're hilarious. And they're so heartrending and they're so earnest and they're so nutty..." —Maira Kalman (18:29)

  • Kalman’s mother grew to love Pete, even cooking for him and knitting him sweaters ("Beautiful Bauhaus pea") ([17:52]).
• On Unconditional Love
  • Kalman attributes a dog’s lovability to their silence and low expectation ([19:06]).

    "The expectation is really just be who you are, and I love you, you know, what more do you need?" —Maira Kalman (19:35)

• Intersection of Word and Image
  • Heavily influenced by the Dadaists and Futurists; text and image are deeply fluid in her storytelling ([20:54]).

    "The intersection of how you play with words and how you play with paintings..." —Maira Kalman (20:54)

3. Barry Blitt: From Hockey Players to Political Satire

• Early Days and Dual Personalities
  • “Reverential” vs. “crazy” drawings; sending work to magazine art directors—funny work often resonated most ([23:00-27:13]).

    "I had a scam going where I would draw hockey players... I would present them with their drawings. And I ended up, you know, befriending a lot of hockey players and getting free tickets..." —Barry Blitt (23:00)

• Reluctance to Cartoonist Label
  • Initially saw “cartoonist” as a slight, sought seriousness but ironic success came through humor ([26:43]).

    "I was trying to do something higher, but I'm not sure what. What it is I was trying to do." —Barry Blitt (26:43)

• Path to The New Yorker and Satire
  • Work for Entertainment Weekly bridged pop culture and politics. The Monica Lewinsky scandal was pivotal in pushing political commentary ([28:31-29:13]).

    "Politics became pop culture... I started being asked... to make Bill Clinton jokes. And politics was everywhere." —Barry Blitt (28:31)

• On Depth vs. Satire
  • Blitt contends he lacks deep political expertise—even as his work resonates on a profound level ([29:26]).

    “It's easy to make jokes about stuff, but to understand it deeply, I don't think I do.” —Barry Blitt (00:06 / 29:26)

• Pitching New Yorker Covers
  • Describes the mystique and serendipity of pitching cover sketches ([32:08]).

    "...the amount of real estate a cover has is intimidating." —Barry Blitt (32:08)

4. Edel Rodriguez: Bravery, Branding, and Confrontation in Illustration

• Pressure, Surrealism, and Activism
  • Known for bold covers and iconic visual metaphors (e.g., Trump as melting/loss of composure). Feels odd sharing award lists with superstars ([37:01]).

    "I'm just always shocked by all of it... It's actually what I've learned is how sometimes simple it is to get to places where you never dreamed you'd be at. If you just kind of work and show it..." —Edel Rodriguez (37:10)

• Origin of ‘Meltdown’ Trump Cover
  • Collaborations with Time art director leveraged his existing visual vocabulary ([38:13]).

    "The trick was to making it work, because you can do a face that has a bunch of details... I really wanted it to just focus on his mouth." —Edel Rodriguez (38:13)

• Agency and Pushing Limits
  • To overcome editorial restraint, Rodriguez built an online following by independently publishing stark, provocative imagery ([42:06]).

    "I was trying to find a way to subvert that process. And the way I found was to get ahead of it, put things out myself, have fan base or people on the Internet sharing..." —Edel Rodriguez (42:06)

• On Confrontation vs. Neutrality
  • Feels artists and media should confront fascism and injustice directly, rather than strive for false "neutrality" ([40:15]).

    "You don't appease fascists. You really do confront it as strongly as possible. And that's what I wanted to do with that cover." —Edel Rodriguez (40:15)

• Speed and Symbolism
  • Often works extremely fast, focusing on symbolism instead of direct likeness ([45:05]).

    "It's more about. It's anti branding. It's creating a brand and then doing everything to destroy it, basically." —Edel Rodriguez (45:31)

5. Christoph Niemann: The Discipline and Mystery of Conceptual Illustration

• Concept above Craft
  • Chooses projects where the core is a strong idea, not just the execution ([46:39]).

    "My talents would be more in coming up with a concept and then trying to find a style within my limitations to make it come alive." —Christoph Niemann (46:39)

• Value of Limitations
  • Believes artistic limits can spark creativity; the “off” details create surprises ([47:08-47:50]).

    "...in that limitation, interesting stuff happens. Because what makes a drawing... interesting is that something unexpected is happening." —Christoph Niemann (47:08)

• The New Yorker Cover ‘Contest’
  • Getting a cover is never certain; it’s more about persistence and luck than hierarchy ([48:43-50:16]).

    "You can increase luck by just trying a lot, and that will increase your chances for luck to work out." —Christoph Niemann (50:16)

• On Playfulness and Creative Anguish
  • A playful product often comes from a difficult, tense creative process ([51:20]).

    "A drawing that has a very swift feel, you have to... it really has to come in one swoop... the sixth one might ruin the whole drawing." —Christoph Niemann (53:05)

• Creative Doubt as Fuel
  • Identifies with universal creative anxieties: irrelevance, self-doubt, dryness of ideas ([53:34-54:50]).

    "The most wonderful thing about our profession is that we cannot repeat ourselves." —Christoph Niemann (00:11 / 54:28)

Notable Quotes & Memorable Moments

• “It’s easy to make jokes about stuff, but to understand it deeply, I don’t think I do.”
  —Barry Blitt ([00:06] / [29:26])

• “Just be who you are, and I love you. You know, what more do you need?”
  —Maira Kalman ([00:49] / [19:35])

• “The most wonderful thing about our profession is that we cannot repeat ourselves.”
  —Christoph Niemann ([00:11] / [54:28])

• “You do your sketches, you get to a point and they’re like, whoa, whoa, whoa, that’s too much. That’s too strong. And it gets dialed back.”
  —Edel Rodriguez ([00:42] / [42:06])

• “If you have both good ideas and good style, your career is maybe a bit longer.”
  —Brian Rea ([06:32])

Segment Timestamps

| Segment | Time Marker | |---------------------------------------------------|---------------| | Intro & theme set by Debbie Millman | 00:18 | | Brian Rea interview begins | 04:17 | | Brian Rea’s early career and advice | 05:18–14:02 | | Maira Kalman interview highlights | 14:26–21:53 | | Barry Blitt interview highlights | 22:22–33:09 | | Edel Rodriguez interview highlights | 36:08–45:53 | | Christoph Niemann interview highlights | 46:09–56:52 |

Summary & Takeaways

This episode is a celebration of not only the longevity of Design Matters but of the enduring, ever-evolving craft of illustration. Each artist shares hard-won wisdom and vulnerability about creative risk, industry pressures, the balance between style and concept, and the necessity of confronting both internal doubts and external realities.

The tone is reflective, honest, and often humorous—showing that behind iconic visuals are practitioners deeply aware of their social role, yet never losing sight of the personal and unpredictable journey that is essential to creativity.

For full interviews and more insights into their lives and works, visit designmatters.com