AUGUST 17 • 2023 | 69

child’s sensibility, simultaneously 
making his audience relive the 
innocence of being a kid and 
undermining it from an edgy 
adult distance. 
Thirty years later, I had anoth-
er disorienting Pee-wee moment. 
I attended a screening of Nancy 
Spielberg’s 2014 documentary on 
American airmen who fought 
in Israel’s war of independence, 
Above and Beyond. Suddenly, 
there was Paul Reubens again, 
seated beside his mother and 
explaining how his father, Milton 
Rubenfeld, was an American 
pilot who volunteered in the 
fight for Israel. The film recounts 
how his father flew in a critical 
mission against the Iraqi army 
and was shot down over the 
Mediterranean (he survived).
“He was swaggering and 
macho, like Indiana Jones,
” 
Reubens says. “He felt like it was 
his destiny.
”
I hadn’t even considered 
until then that Reubens was 
Jewish. In Why Harry Met Sally: 
Subversive Jewishness, Anglo-
Christian Power, and the Rhetoric 
of Modern Love (2017), one of 
the few books about Jewish com-
edy in which Reubens appears, 
Joshua Louis Moss groups him 
with a cohort of Jewish comics 
whose acts were “nearly com-
pletely devoid of references to 
either their Jewish background 
or Jewish culture more generally.
” 
Paul Reubens died July 30, 
2023, at age 70; a publicist said 
he “privately fought cancer for 
years.
” And even though his 
career was derailed by scandal 
— he was arrested for “exposing” 
himself at a porn theater in his 
hometown of Sarasota, Florida, 
in 1991 — it’s not a stretch to 
remember him as an heir to 
the masterful comics who mined 
Jewish comedy’s more anarchic 
vein. 
Like the Marx Brothers, Pee-
wee — with a crewcut, a too-
tight suit, a red bow tie and a 
hint of lipstick and rouge — was 

a costumed agent of chaos when-
ever he bumped against straight 
(in all senses of the word) char-
acters. Like Jerry Lewis, his char-
acter seemed stuck in pre-ado-
lescence, but with an adult libido. 
He could be as sexually ambig-
uous as Milton Berle in one of 
his cross-dressing bits. And you 
could even connect him to Baby 
Snooks, the little-girl character 
created by Fanny Brice of Funny 
Girl fame.

HIS EARLY YEARS
Paul Rubenfeld was born Aug. 
27, 1952, in Peekskill, New York, 
and grew up in Sarasota. Milton 
and his wife Judy (Rosen) owned 
a lamp store. Milton Rubenfeld 
had been a top fighter pilot who 
served in the Royal Air Force, 
and then the U.S. Army Air 
Force, during World War II. He 
became one of five Jewish pilots 
who flew in smuggled fighter 
planes and helped establish the 
Israeli Air Force.
“When I was a youngster, they 
seemed like fish stories to me,
” 
Reubens recalled in the Spielberg 
documentary. “I didn’t have any 
real perspective on it until Ezer 
Weizman [an Israeli Air Force 
general and seventh president 
of Israel], I believe, was the first 
book that actually mentioned 
my dad by name. And all of a 
sudden, all these stories I’
d heard 
my whole life growing up were in 
this book. Once I actually knew 
he really did all those things, 
and then they weren’t things 

everyone else did, I just had a 
completely different view of [my 
father].
”
After studying at Boston 
University and the California 
Institute for the Arts, Paul creat-
ed the Pee-wee character in the 
late 1970s as a member of the 
Los Angeles improv troupe The 
Groundlings. HBO produced 
a successful special starring the 
character, and Pee-wee became 
a cult figure, appearing on talk 
shows and often confusing the 
hosts with his child-like deliv-
ery and pansexual (or perhaps 
pre-sexual) persona. (David 
Letterman had him on his show 
regularly but never seemed 
completely comfortable in his 
presence.)
His first feature film, Pee-wee’s 
Big Adventure (1985) was direct-
ed by Tim Burton (who would 
go on to direct Beetlejuice and 
one of the best of the Batman 
reboots) and was a financial and 
critical hit. A sequel, Big Top Pee-
wee (1988), was less successful 
but had its moments. 
From 1986 through 1990, 
Reubens starred in 45 episodes 
of the CBS Saturday-morning 
children’s program Pee-wee’s 
Playhouse. It was both a chil-
dren’s show and a send-up of 
a children’s show, featuring a 
recurring cast of characters that 
included a sea captain (Phil 
Hartman), a cowboy (Laurence 
Fishburne), a “mail lady” (S. 
Epatha Merkerson) and a talking 
chair. More than one critic noted 

Reubens’ debt to Soupy Sales, 
another Jewish comedian whose 
1960s kids show also managed 
to appeal to children as well as 
adults who were in on the joke. 
The indecent exposure arrest 
led to a media frenzy that made 
it impossible for Reubens to con-
tinue playing a children’s enter-
tainer. He eventually emerged 
in a series of cameos and small 
roles in film and television 
shows — including a memorable 
term as a grotesquely inbred 
Hapsburg prince on 30 Rock, 
and as a drunken Pee-wee oppo-
site Andy Samberg in a 2011 
Saturday Night Live video.
In 2010, he revived the char-
acter that made him famous 
on Broadway in The Pee-wee 
Herman Show, and in 2016, 
he co-wrote and starred in the 
Netflix original film Pee-wee’s Big 
Holiday.
Reubens kept his health issues 
private. “Please accept my apolo-
gy for not going public with what 
I’ve been facing the last six years,
” 
he said in a statement distributed 
by his publicist after his death. “I 
have loved you all so much and 
enjoyed making art for you.
”
In a 1987 Rolling Stone inter-
view, Reubens acknowledged 
those who said his act built on 
the Jewish comedians who came 
before him, including Eddie 
Cantor, the former vaudevillian 
who played a frenetic, wide-eyed 
innocent in a series of popular 
movie comedies of the 1930s. 
“Jerry Lewis I saw when I was 
little,
” he said. “Soupy Sales I 
probably saw when I was young-
er. I never knew who Eddie 
Cantor was until years later, 
when a lot of older people used 
to go [in an old Russian-Jewish 
furrier’s accent], ‘You’re like a 
young Eddie Cantor.
’ I started to 
watch Eddie Cantor, and I could 
definitely see the resemblance. 
His movies are just incredible, 
very fantasy oriented and come-
dy oriented.
” 

Paul Reubens 
performs as Pee-
wee Herman in 
Chicago in 1983. 

PAUL NATKIN/GETTY IMAGES VIA JTA

