Welcome back to The Deep Dive. Today we are really
digging into someone quite remarkable, Wanda
Sykes. I mean, she's consistently sharp, incredibly
versatile, and frankly, just fearless. Absolutely,
a true force. Her career, it spans stand -up,
acting, writing, producing. And activism, too.
Deeply committed activism. It really is amazing
when you list it all out. So many hats, right?
And she wears them all so well and often at the
same time. Exactly. I mean, she's an Emmy -winning
writer. Right now, she's co -creator and executive
producer of The Upshaws on Netflix. And you might
remember, Entertainment Weekly called her one
of the 25 funniest people in America way back
in 2004. Yeah, 2004. That's longevity right there.
So our mission today, our deep dive goal, is
sort of tracing that whole trajectory. Where
did this incredibly uncompromising voice come
from? And how has she managed to keep that huge
professional success going while also being so,
well, politically potent? It's a balancing act.
Yeah, definitely. We've got sources covering,
you know, the big career milestones, her personal
story, and honestly, some seriously surprising
origin details. Things that just make you rethink
the phrase unconventional background. Let's maybe
start with the recognition. That really sets
the stage for how comprehensive her approach
to comedy has always been. Good idea. That Emmy
win you mentioned, it came pretty early, right?
1999? Yeah, for outstanding writing for a variety
music or comedy special. That was for her work
on The Chris Rock Show. And that win tells you
something crucial. She was a writer, a powerhouse
writer, long before most people knew her face,
you know? That's the key point, absolutely. She
wasn't just like... a comic reading line someone
else wrote, she was generating the material,
material that really helped to find late 90s
political satire. Right. But to really get the
full picture, to appreciate how sophisticated
she became as a writer and later a producer,
we have to talk about the big surprise, the one
detail that makes everyone pause. The wait, what
moment? Exactly. Here's where it gets really
interesting. Before the Emmys, before the writers
rooms, before she was even doing stand up on
like Def Comedy Jam, Wanda Sykes had this incredibly
sensitive, very structured, high level government
job. She worked for five years, get this, as
a contracting specialist at the National Security
Agency. The NSA. The NSA. It's just the contrast
is wild, isn't it? Totally jarring. You go from
like classified documents and government procurement.
Uh -huh. Bureaucracy. Rules. Structure. To the
world of stand -up comedy. Which is, you know,
chaotic, often unpredictable, definitely not
classified. And it wasn't just a quick internship
or something. Five years. That's a serious commitment.
She was deep in the logistics, vendor management,
the really complex procurement stuff needed to
keep a massive intelligence agency functioning.
So she had this highly organized, systematic
brain trained in, well, government work. Exactly.
Which she then turned around and applied to,
you know. writing jokes and eventually running
entire TV shows. It's quite the pivot. I just
love the image of her like doing a set at some
DC open mic, maybe that Coors Light super talent
showcase they mentioned on a Friday night. Yeah.
And then Monday morning, she's back at her NSA
desk managing contracts. It's like two completely
different lives colliding. It really shows incredible
discipline, doesn't it? Holding down that serious
career while simultaneously finding her true
voice, her comedic voice. Which leads us perfectly
into the foundation. Her early life, those roots,
which are also pretty surprising in their own
way. Right. So Wanda Yvette Sykes, born March
7, 1964, in Portsmouth, Virginia. OK. And her
family life, very structured, as you might guess
now. Her father, Harry Ellsworth Sykes, was a
U .S. Army colonel, worked at the Pentagon. Wow.
OK. High level. And her mother, Marion Louise,
was a banker. So you've got military discipline,
financial structure. That kind of environment
definitely instills a sense of order. And the
family moved to Maryland when she was young,
third grade, I think. Yeah, attended Arundel
High School in Gambrills. And that structure
carried right through her education. She went
to Hampton University. Got a Bachelor of Science
degree in marketing. Exactly, marketing. That's
it. And she was in the Alpha Kappa Alpha sorority.
Again, this isn't the typical path you imagine
for a groundbreaking comedian. It sounds more
like someone aiming for a corporate track or,
well. Or government success, which is exactly
where she ended up initially. Precisely. That
BS in marketing. It led straight to the NSA.
And just to elaborate a bit on that role, contracting
specialist. Yeah. What does that really mean?
It's essentially being a logistics expert, but
on a massive scale, handling large, often very
sensitive procurement decisions. Buying hardware,
managing services from vendors, making sure everything
complies with, you know, endless regulations.
So skills like organization, negotiation, paying
attention to tiny details. Invaluable skills,
especially if you later decide to become, say,
an executive producer running a complex network
television show. That's a brilliant connection.
I hadn't really thought about how those NSA skills
might translate directly to Hollywood production.
It's not a stretch at all. Managing budgets,
timelines, people. It's project management, just
in a different field. Okay, that NSA period makes
a different kind of sense now. But speaking of
deep foundations, we have to talk about that
genealogy piece, the thing from the PBS show,
Finding Your Roots. Oh, absolutely. That was...
That was stunning. Truly unique history, not
just for her family, but for American history,
period. So they traced her ancestry way, way
back, right, to the 17th century. Yes, specifically
to a 1683 court case in Virginia. It involved
her ancestor, a woman named Elizabeth Banks.
And Elizabeth Banks was. She was a free white
woman, but also an indentured servant. Correct.
And the case came about because Elizabeth gave
birth to a biracial child. a daughter named Mary
Banks. The father was an enslaved man. Okay,
and this is where the legal stuff gets really
crucial, especially for that time period. Hugely
crucial. Because in colonial Virginia, the laws
were solidifying around the idea that a child's
status followed the mother. But it was still
early days. And in this specific documented case...
Mary Banks, the daughter, inherited her mother's
free status. Exactly. Despite the father being
enslaved, Mary was legally free because her mother
was free. This set a vital legal precedent at
that time. So Wanda Sykes' family line, going
back centuries, was rooted in documented freedom,
even against the backdrop of slavery and, you
know, immense social and legal pressure. Right.
It's an unbroken line of freedom traced back
to the late 1600s. And the historian they quoted,
Ira Berlin, he specializes in American slavery.
His quote was incredibly powerful. He said, Sykes'
family history is, and I'm paraphrasing slightly,
the only such case that I know of in which it
is possible to trace a black family rooted in
freedom from the late 17th century to the present.
The only one he knows of. That's staggering.
It provides this incredible historical context,
doesn't it? For the kind of freedom, and frankly,
the uncompromising nature you see in her comedy
today. Her willingness to speak truth to power,
to be absolutely herself. Maybe it's not just
a personality trait. Maybe it's ancestral. Wow.
That's a powerful thought. Okay, so her background
is this mix of intense structure, the NSA years,
and this deep, resilient history. How did she
make the actual leap? From contracting specialist
to comedian. Well, it wasn't overnight. It was
gradual. She started doing stand -up back in
1987. While still at the NSA. Right, at those
talent showcases in D .C., like the Coors Light
one. So she had about five years of practicing,
doing gigs nights and weekends, basically honing
her craft without the immediate pressure of needing
comedy to pay the bills. Smart way to do it,
really. De -risked it a bit. For sure. But then
came the big decision, 1992. She leaves the NSA.
Grits the stable government job. And moves to
New York City to pursue comedy full -time, which,
as any comic will tell you, is a massive leap
of faith, trading security for, well, chaos and
uncertainty. But she started getting noticed
pretty quickly in New York. Yeah, she got some
important early TV spots. Russell Simmons' deaf
comedy jam was huge back then. It put her sharp
delivery, her perspective, in front of a big,
influential audience. And then came the connection
that really changed things. Opening for Chris
Rock. At Caroline's Comedy Club. That was the
first major break, the one that led directly
to the next step. Which was joining the writing
team for the Chris Rock show on HBO in 97. Exactly.
And she wasn't just writing. She was on screen
a lot, too, doing sketches, playing different
characters. That's critical development time,
mastering joke structure in the writer's room,
and mastering timing and delivery on stage all
at once. And that all led to the Emmy win in
1999. You have to remember what that show was
like. Oh, yeah. The Chris Rock show was smart.
It was political. It was doing cutting -edge
cultural satire. She was right in the thick of
a creative process that demanded rigorous thinking
and honestly fearless commentary. So that NSA
-trained, organized mind probably meshed perfectly
with the need to be provocative and sharp in
the writer's room. I think so. It's that synthesis
again. Structure meets artistic rebellion. Let's
unpack the comedy style that really came out
of that period. It's described in so many ways.
Observational, surreal, insult comedy. Black
comedy, blue comedy, satire. It's a wide range.
But what does that list actually mean in practice?
How does she use those different tools? Well,
I think it means she starts with a... Familiar
observational stuff about relationships, daily
life, you know. But she always injects it with
this political edge, this perspective rooted
in her identity as a black woman in America.
Right. So even when she's using, say, blue comedy,
which can sometimes just be for shock value,
she's usually doing it for a reason. Often, yeah.
to satirize hypocrisy or maybe societal hangups
about sex or race. It pushes a point home, makes
it sharper. It's not just jokes for joke's sake.
And the subjects she tackles are huge. American
politics, obviously. African -American culture,
pop culture, racism, sexism, relationships. Human
sexuality traditions. Pretty much everything.
Her stand -up specials are incredibly dense with
this stuff. If you go back to her early 2000s
material, she used these almost surreal setups
to get at races. It's not just the obvious stuff,
but the microaggressions, the everyday absurdities.
Exactly. She has this amazing gift for taking
those interactions, the ones that are frustrating
or confusing or just... plain weird and turning
them into punchlines that are both hilarious
and make you think, oh, yeah, I get that. And
that versatility, moving from jokes about her
kids one minute to like biting satire about Congress
the next. That's why she stayed relevant for
so long, wouldn't you say? Absolutely. She's
always challenging the audience. Yeah. Making
you laugh, sure, but also making you think. Yeah.
It's never passive viewing with her specials.
And that mastery, that unique voice, it led very
quickly to her becoming almost ubiquitous across
TV, film, voice acting. Which brings us to the
next phase, her dominance on screen. Yeah, she
clearly understood that to really build a lasting
career, she needed to move beyond just the stand
-up stage. And those TV roles starting in the
2000s really cemented her place in the mainstream,
often in quite different ways. Let's talk Curb
Your Enthusiasm. That was a long recurring role,
2001 to 2011, playing herself. Which is such
an interesting role on that show. Because in
Larry David's universe of awkwardness and neurosis,
Wanda was often the only one who saw right through
his nonsense and just called him on it. Totally.
She was like the voice of reason or maybe the
voice of justified exasperation. Exactly. She
functioned almost as this unshakable moral compass.
The one character who absolutely refused to play
by Larry's ridiculous unwritten social rules.
It's kind of a recurring theme for her actually
being the one who speaks the truth, even when
it's super uncomfortable. And doing it in a largely
improvised setting like Curb that takes incredible
comedic intelligence, just lightning fast wit.
For sure. Then she tried the more traditional
sitcom route herself with Wanda at Large on Fox
in 2003. That one was pretty short -lived though.
Right. But her biggest mainstream sitcom success
was probably The New Adventures of Old Christine.
Definitely. 2006 to 2010. Playing Barb, opposite
Julia Louis -Dreyfus. She started recurring,
then became a series regular. That really established
her as this reliable, funny presence in a more
conventional network comedy format. It did. But
then years later, you see her guest roles and
they really showcase her range, her ability to
adapt to very specific comedic tones. Like the
Emmy nominations she got for Outstanding Guest
Actress for Black -ish a couple of times. Right.
2017 and 2018. And maybe even more impressively,
playing Moms Mabley on The Marvelous Mrs. Maisel
in 2020. Playing Moms Mabley, that's portraying
a comedy legend, a real pioneer. That requires
more than just being funny. It requires research,
embodying a historical figure. Absolutely. It
showed real dramatic and comedic depth. But going
back to her current work, her commitment to being
behind the camera as well as in front is clear.
You mean the Upshaws on Netflix, where she stars
as Lucretia Turner? Yes, but crucially, she's
also listed as co -creator, writer, and executive
producer. Ah! There's that NSA trained mind again.
Exactly. Executive producing a major comedy like
that. It's managing budgets, schedules, people,
creative vision. It demands that same logistical
skill set. She has real control over the story
and the tone. Blending family comedy with that
sharp social relevance she's known for. And alongside
all this TV work, her film career was taking
off too, giving her huge visibility. Yeah, big
live action roles. Monster -in -Law in 2005,
that was a hit. My Super Ex -Girlfriend in 2006.
Then those family comedies like Evan Almighty
and License to Wed in 2007. She was popping up
everywhere for a while there. And more recently,
people definitely know her from the Bad Moms
movies. Oh yeah, Dr. Carl. The therapist. Right.
In both Bad Moms 2016 and A Bad Mom's Christmas
2017, she just steals every scene she's in. Her
ability to just drop into an ensemble cast and
make her lines the funniest ones with that dry
delivery. It's mastery is comedic timing. Okay,
but we absolutely cannot skip over her voice
work. The sheer volume of it is incredible. It
really is. She's leveraged that distinctive voice
into becoming, honestly, one of the most reliable
and recognizable voice actors out there, especially
in animation. The list is long. Stella the Skunk
in Over the Hedge. Yep, 2006. Bessie the Cow
in Barnyard, both the movie and the TV series
that followed. And probably the biggest one for
a lot of families, Granny in the Ice Age movies.
Yes, the grumpy, hilarious sloth. She was in
two of the sequels. Continental Drift and Collision
Course, those are massive global franchises.
Her voice was a key part of their comedy. It's
amazing how her voice works for both kids' movies
and, you know, much edgier stuff, like Gladys
Murphy on Crank Yankers. Right, the puppet prank
call show. The original run in the revival. And
she even jumped into Star Wars recently, voicing
Fee Genoa in The Bad Batch. Wow. From Ice Age
to Star Wars, that's incredible range. It just
shows her marketability. That voice carries this
specific weight. It could be sarcastic, warm,
observant, sometimes all at once. It makes her
perfect for pretty much any genre, from G -rated
animation to R -rated satire. Okay, so we've
covered her incredible output, stand -up, writing,
acting, producing, voice work. Now let's pivot
a bit. Let's talk about the moments where Wanda
Sykes, the public figure, the voice of opinion,
really came into focus. Ah, right. The times
when her political views, her sense of integrity,
put her right in the spotlight. Late night hosting,
controversies, those principled stands she's
taken. She had experience hosting, right? Like
Comedy Central's Premium Blend way back. Yeah,
she did. But her own big shot at late night was
the Wanda Sykes show on Fox, ran 2009 to 2010.
And that show had a specific format, didn't it?
Aimed at political comedy. Yeah, it was structured
kind of like Bill Maher shows, a monologue, then
a panel discussion about current events. It was
clearly positioning her as a major voice in that
space, trying to blend her stand -up wit with
topical analysis. And just before that show launched,
she landed a really high -profile, high -pressure
gig. The White House Correspondents Association
Dinner, May 2009. Featured entertainer. Which
was a huge deal in itself. She was the first
African -American woman to do it and the first
openly LGBT person in that role. Absolutely groundbreaking.
Cedric the Entertainer was the first African
-American man back in 2005, but she broke multiple
barriers that night. But the night is often remembered
for, well, something else. A specific joke. The
Rush Limbaugh joke. Yeah. Yeah. This was pretty
soon after President Obama had taken office and
Limbaugh had famously said he hoped Obama would
fail. And Sykes's response during her set was
intense. It was pure, uncut Wanda Sykes insult
comedy delivered on the biggest political stage
imaginable. She quipped something like Rush Limbaugh
said he hopes he fails. I hope his kidneys fail.
How about that? And then added something about
waterboarding. Whoa. Yeah, that. That did not
go over quietly. No kidding. Massive public backlash,
nonstop media coverage. It was incredibly controversial.
And it really highlighted her style, didn't it?
Willing to use aggressive, even blue humor against
a powerful political opponent right there in
front of the president, the press corps, everyone.
It absolutely cemented her reputation. This is
a comic who will push boundaries, who will risk
alienating people to make a political point she
believes in. No fear. It was a definite professional
risk. But as we've seen, she seems to prioritize
her integrity over playing it safe. Which brings
us to another major live TV moment much more
recently. The 2022 Oscars. Co -hosting with Regina
Hall and Amy Schumer. And finding herself right
in the middle of the Will Smith -Chris Rock slap
incident. Right. And given that Chris Rock was
her friend, her former boss from the HBO show.
Her reaction was pretty strong and immediate.
Very strong. She publicly criticized the Academy
for letting Will Smith stay in the room after
the slap, enjoy the rest of the show, and then
accept his award. She used words like gross,
right? Saying it sent the wrong message. Exactly.
She said for the Academy to let him stay. I was
like, how gross is this? This is just the wrong
message. Her stance was clear. Assault happens,
you get removed. End of story. It was about professional
conduct and the signal it sent. And that sense
of professional integrity, standing up for what
she thinks is right, wasn't just about reacting
to live events. It affected her career choices
directly, like her exit from the Roseanne revival.
Ah, yes. 2018, she was the head writer for that
10th season revival. A huge, high -profile, presumably
well -paying job. But then the star, Roseanne
Barr, posted that infamous tweet, the racist
one about Valerie Jarrett. And Sykes' response
was immediate. No waiting, no hesitation. She
announced on Twitter, May 29, 2018, that she
would not be returning to the show. Before ABC
even canceled it, that's key. She quit first.
Yes. She walked away from a massive gig, a powerful
role, purely based on principle. Standing against
speech, she found reprehensible. It just confirmed,
yet again, this pattern. career comes second
to her core values. So from the White House dinner
to the Oscar stage to the writer's room, it's
a remarkably consistent ethical line. She doesn't
seem to separate her job from her conscience.
Not at all. Which makes her one of the most reliably
outspoken and frankly trustworthy political voices
we have in entertainment. OK, let's transition
out to her personal journey, her coming out,
her family, her health, which, of course, is
all deeply tied into her activism as well. Right.
So she was married before in the 90s. to a record
producer named Dave Hall. But the major personal
shift, the one that became public, happened later.
She married her wife, Alex Nebalski, who's French,
in October 2008. Yes. And then, just one month
later, November 2008, she publicly came out as
a lesbian. And the timing and setting were significant,
weren't they? Very. She came out while speaking
at a same -sex marriage rally in Las Vegas. It
was specifically about California's Proposition
8, which aimed to ban same -sex marriage. So
her public coming out was intrinsically linked
to a political fight she cared deeply about.
Wow. So it wasn't just a personal announcement.
It was an act of political activism itself. Pretty
much. And then shortly after... April 2009, she
and Alex welcomed fraternal twins. So the public
declaration, the fight for marriage equality,
and the creation of her family all happened very
close together. It really underscores the urgency
she must have felt. But the journey to acceptance
wasn't necessarily smooth, even within her own
family. No, and she's been open about that. She
actually came out to her parents back in 2004
when she was 40. And initially, her parents,
who came from that more conservative, structured
background we talked about, They really struggled
to accept her homosexuality. To the point where
they didn't attend her wedding. Right. Which
caused a period of estrangement, which sounds
incredibly painful. It's a reminder that even
for successful, confident public figures, family
acceptance can be a difficult process. Have they
reconciled since then? Yes. The sources say they
have, thankfully. But sharing that story highlights
the personal cost that sometimes comes with living
authentically. Beyond her family life, she's
also used her platform when it comes to her health
in a really powerful way. Yes. In 2011, she went
on the Ellen DeGeneres Show and announced she'd
been diagnosed with DCIS, ductal carcinoma in
situ. Which is described as a non -invasive stage
zero breast cancer. Correct. And facing that
diagnosis, she made another significant choice
and chose to share it. She opted for a bilateral
mastectomy to significantly lower her risk of
developing invasive cancer in the future. And
by being so open about it. She became this incredibly
effective, though maybe accidental, advocate
for women's health, encouraging proactive screening,
discussing preventative options, using her own
vulnerability to potentially help others. Her
more formal activism goes deep, too, right? Especially
around LGBTQ plus issues. Oh, yeah. She was,
as she said. devastated when Prop 8 passed in
California. She threw herself into the fight
for marriage equality, hosting events, emceeing
fundraisers, really using her voice and visibility.
And her activism isn't limited to just that one
issue. Not at all. She's worked with PETA on
promoting anti -chaining laws for dogs in her
home state. Animal welfare is clearly important
to her. And she supports the Ruth Ellis Center
in Detroit. Yes, which is a vital organization
providing support and services for homeless or
at -risk LGBT youth. That shows a commitment
to the most vulnerable parts of the community.
And she uses her platform constantly, right,
like on Twitter? Definitely. Promoting specific
political actions, like urging Congress to pass
voting rights legislation, like the Hashtag For
the People Act, or commemorating civil rights
icons like John Lewis. She understands her platform
is a tool for social and political engagement.
She truly is an entertainer who walks the walk
when it comes to advocacy. And that combination
of talent and commitment has brought her a lot
of recognition over the years from different
spheres. Which brings us neatly to the last part,
awards and discography. We mentioned the 1999
Emmy win for writing, but her standup itself
has earned major awards too. For sure. She won
the American Comedy Award way back in 2001 for
funniest female standup comic. That's pure recognition
early on. And then there are awards recognizing
her impact beyond just comedy. Exactly. GLAD
gave her the Stephen F. Kolzak Award in 2010.
That award specifically honors LGBTQ plus media
professionals who have made a significant difference
in promoting acceptance. And more recently, is
she still getting that kind of recognition? Absolutely.
She's actually set to receive the Critics' Choice
Association's Celebration of LGBTQ Plus Cinema
and Television Career Achievement Award in 2025.
These aren't just trophies. They acknowledge
decades of impact on visibility and culture.
And her stand -up is still getting nominated
for major awards, right? Yes. Just this year,
2024, she got a Golden Globe nomination for Best
Performance in Stand -Up Comedy on Television.
That was for her latest Netflix special, Wanda
Sykes. I'm an entertainer. It proves she's still
at the absolute top. Top of her game, still relevant,
still cutting edge. You can really trace her
evolution by looking at her specials over the
years. Definitely. It starts with Tongue Untied
back in 2003. Then those two big HBO specials,
Sick and Tired in 2006, which was huge. And I'm
a Beamee in 2009. Then later came What Happened,
Miss Sykes in 2016. And not normal on Netflix
in 2019. That's the one that got recent Emmy
nods too. Right. And don't forget the book. Yeah,
I said it. From 2004, a collection of her humorous
observations. It just reinforces again that she's
fundamentally a writer, a generator of sharp
content, not just a performer. It's that combination,
isn't it? The literary skill, the sharp writing.
Combined with that absolute fearlessness on stage,
she crafts the material with that disciplined
mind, maybe honed back at the NSA. Huh, maybe
so. And then delivers it with all the emotional
weight and historical resonance of someone deeply
committed to speaking their truth. Okay, so.
Let's try to wrap this all up. What's the final
takeaway from this deep dive into Wanda Sykes?
We've gone from the NSA. Right. A highly structured,
bureaucratic government job. All the way to comedy
legend, Emmy winning producer, voice acting star
and highly visible, deeply principled activist.
I think the synthesis is that Wanda Sykes has
somehow mastered this incredible balancing act
between professional success, mainstream bankability.
I mean, she's granny and I. You can't get much
more mainstream than that. Or Dr. Carl in Bad
Moms. Hollywood clearly trusts her to deliver
commercially. Exactly. But at the same time,
she is absolutely relentless and uncompromising
in her political commentary and her personal
integrity. The Limbaugh joke. The Oscars condemnation.
Walking away from Roseanne. These aren't small
things. They define her as someone who will not
back down, even if it might hurt her career.
It's a really delicate high wire act. She's been
walking for decades. And she proves that maybe
you don't have to choose. You don't have to pick
between having massive corporate success and
being a genuine, fearless voice for change or
dissent. Maybe that discipline she learned early
on, that structure, allows her to manage the
complexity of wearing all those hats. I think
that's a huge part of it. She seems uniquely
equipped to handle both the demands of the industry
and the demands of her conscience. So that leaves
us with a final thought, something for you, the
listener, to maybe chew on. In today's world,
which feels so polarized, so divided, can entertainers
maintain that kind of broad success across so
many platforms while also being so consistently,
unapologetically outspoken on political and social
issues? Or is pulling off that constant, delicate
balance, is that itself Wanda Sykes' greatest,
most challenging performance? It's a fascinating
question. She hasn't just shown it's possible.
She's practically written the playbook on how
to do it. Her career really is an incredible
case study. How those foundational skills, that
structure, combined with an absolutely unwavering
moral compass can fuel decades of relevance and
impact. Truly remarkable. That was the deep dive
into the extraordinary career of Wanda Sykes.
Thanks for joining us. We'll see you next time.