Two titans of com­e­dy passed away this week­end, but the deaths of Dick Gre­go­ry and Jer­ry Lewis have seemed like cul­tur­al foot­notes amidst some of the most anx­ious, angry few days in recent U.S. his­to­ry. Gre­go­ry and Lewis are stars of a bygone era, maybe two full gen­er­a­tions behind con­tem­po­rary pop­u­lar rel­e­vance. And yet, in many ways, the mid-20th cen­tu­ry world where both men got their start feels clos­er than ever.

Both Gre­go­ry and Lewis once wield­ed con­sid­er­able pow­er in the enter­tain­ment indus­try and in their oth­er cho­sen spheres of influence—the civ­il rights move­ment and char­i­ta­ble giv­ing, respec­tive­ly. In near­ly every oth­er respect, the two could not have been more dif­fer­ent.

Gre­go­ry broke into main­stream suc­cess with a new wave of black comics like Bill Cos­by and Richard Pry­or, and like Pry­or, he did so by telling painful truths about racism that many white Amer­i­cans laughed about but were unwill­ing to hon­est­ly con­front or change. You can hear an ear­ly exam­ple in the rou­tine above, from his 1962 album Dick Gre­go­ry Talks Turkey.

Gre­go­ry got his big break in 1961 when he seized the moment in a try­out at Hugh Hefner’s Chica­go Play­boy Club. As he lat­er told CBS Sun­day Morn­ing, “I pushed that white boy out of the way and ran up there…. Two hours lat­er, they called Hefn­er. And Hefn­er came by and they went out of their mind.” That same year, he made his first nation­al TV appear­ance. See it at 15:16 in the doc­u­men­tary Walk in My Shoes just above, which also fea­tures Mal­colm X and Con­gress for Racial Equal­i­ty (CORE) founder James Farmer.

In the playlist  below, you can hear three full Gre­go­ry com­e­dy record­ings, Liv­ing Black & White (1961), East & West (1961), and an inter­view album, Dick Gre­go­ry on Com­e­dy. Through­out his career, Gre­go­ry was an uncom­pro­mis­ing civ­il rights activist who was beat­en and arrest­ed in the six­ties at march­es and protests. He was at the 1963 March on Wash­ing­ton, faced down the Klan to help inte­grate restau­rants, and fast­ed to protest the Viet­nam War. In a review of his provoca­tive­ly-titled auto­bi­og­ra­phy, The New York Times described him as “a man who deeply wants a world with­out mal­ice and hate and is doing some­thing about it.”

He also did some­thing about it in com­e­dy. When Jack Paar’s pro­duc­er called him to appear on the show, Gre­go­ry hung up on him. Then Paar him­self called, and Gre­go­ry told him he wouldn’t come on unless he could sit on the couch, a priv­i­lege afford­ed white comics and denied their black coun­ter­parts. Paar agreed. “It was sit­ting on the couch,” he said, “that made my salary grow in three weeks from $250 work­ing sev­en days a week to $5,000 a night.” For the next sev­er­al decades, he lever­aged his wealth and fame for human­i­tar­i­an and civ­il rights caus­es, and even a run for may­or of Chica­go in 1967 and a pop­u­lar write-in pres­i­den­tial cam­paign in the 1968 elec­tion. He died at 84 a ven­er­at­ed elder states­man of stand-up com­e­dy and of the Civ­il Rights Move­ment.

Jer­ry Lewis’s lega­cy is much more com­pli­cat­ed, and serves in many ways as a “cau­tion­ary tale,” as Nick Gille­spie puts it, for the hubris of celebri­ty. Lewis broke through in the 50s as the ani­mat­ed, rub­bery com­ic foil to Dean Martin’s suave straight man in the huge­ly famous com­e­dy duo of Mar­tin & Lewis. See them above do a standup rou­tine in 1952 on their Col­gate Com­e­dy Hour, with an intro­duc­tion (and inter­ven­tion) from Bob Hope. The act was a phe­nom­e­non. “Com­ing from lit­er­al­ly nowhere,” writes Shawn Levy at The Guardian, “the pair rode a sky­rock­et­ing 10-year career that made them sta­ples of Amer­i­can show­biz for the rest of their lives…. They met when they were just two guys scuf­fling for a break in Times Square, and they helped forge a new brand of pop­u­lar enter­tain­ment suit­ed to the post­war mood.”

In the same year as the broad­cast fur­ther up, Lewis made his first appear­ance, with Mar­tin and Jack­ie Glea­son, on the Mus­cu­lar Dys­tro­phy Asso­ci­a­tions of Amer­i­ca (MDAA) telethon. Just above, see them do a bit while the famil­iar banks of oper­a­tors stand by behind them. Lewis began host­ing his own MDAA telethon in 1966 and did so until 2010, rais­ing bil­lions for the orga­ni­za­tion, which remem­bers him as a “Com­ic genius. Cul­tur­al icon. Human­i­tar­i­an.” Many dis­abil­i­ty activists feel oth­er­wise, includ­ing many for­mer “Jerry’s Kids,” his “pet name,” writes Gille­spie, for the poster chil­dren he recruit­ed to rep­re­sent the MD com­mu­ni­ty on the telethon and relat­ed advo­ca­cy mate­ri­als. “The telethon was wide­ly par­o­died,” and Lewis’s efforts have been seen by many activists and pro­tes­tors as self-serv­ing, per­pet­u­at­ing harm­ful, demean­ing atti­tudes and encour­ag­ing pity for MD suf­fer­ers rather than accep­tance and social equal­i­ty.

As a movie star, Lewis often played an all-Amer­i­can doo­fus whose phys­i­cal antics and stam­mer­ing, boy­ish per­sona endeared him to audi­ences (see above, for exam­ple, from 1952’s Sailor Beware). As a direc­tor, he made tight­ly chore­o­graphed mad­cap come­dies. He also trad­ed in offen­sive stereo­types, par­tic­i­pat­ing in an ugly Hol­ly­wood tra­di­tion that emerged from anti-Chi­nese big­otry of the 19th cen­tu­ry and anti-Japan­ese World War II pro­pa­gan­da. (Lewis was unflat­ter­ing­ly remem­bered in The Japan Times as the “king of low-brow com­e­dy… for­ev­er squeal­ing, gri­mac­ing and flail­ing his way” through var­i­ous roles.) He intro­duced Asian car­i­ca­tures into his act in the Mar­tin & Lewis days (see below) and reprised the shtick in his crit­i­cal­ly-loathed 1980 film Hard­ly Work­ing, in which, writes Paul Maco­v­az at Sens­es of Cin­e­ma, he “real­izes an offen­sive, pro­found­ly racist yel­low-face sashi­mi chef.”

“I imag­ine that most view­ers will be trou­bled by it,” Maco­v­az com­ments, “wrenched vis­cer­al­ly from their enjoy­ment of the Lewisian idiot and pressed squirm­ing into the overde­ter­mined con­cep­tu­al nar­ra­tive zone of Amer­i­can Ori­en­tal­ism.” Those view­ers who know anoth­er of Lewis’s lat­er-career dis­as­ters will rec­og­nize anoth­er awk­ward char­ac­ter in Hard­ly Work­ing, the sad-faced clown of 1972’s dis­as­trous The Day the Clown Died, a film so ill-advised and bad­ly exe­cut­ed that Lewis nev­er allowed it to be released. (Just below, see a short doc­u­men­tary on the abortive effort.)  In the movie, as com­e­dy writer Bruce Handy not­ed in a 1992 Spy mag­a­zine arti­cle, the come­di­an plays “an unhap­py Ger­man cir­cus clown… sent to a con­cen­tra­tion camp and forced to become a sort of geno­ci­dal Pied Piper, enter­tain­ing Jew­ish chil­dren as he leads them to the gas cham­bers.” Meant to be his first “seri­ous,” dra­mat­ic role, the large­ly unseen film now stands as an arche­typ­al epit­o­me of poor taste—an artis­tic fail­ure that Mel Brooks might have dreamed up as a sick joke.

As Gille­spie points out, Lewis’s last years saw him threat­en­ing to punch Lind­say Lohan and telling refugees to “stay where the hell they are.” Long past the time most peo­ple want­ed to hear them, he per­sist­ed in mak­ing “racist and misog­y­nis­tic jokes” and gave “the most painful­ly awk­ward inter­view of 2016” to the Hol­ly­wood Reporter. He became well-known for ver­bal­ly abus­ing his audi­ences. The run­ning joke that Lewis was beloved by the French, which “only made him less respectable in his home coun­try,” may have been run into the ground. But in the lat­ter half of his career, it sums up how much Amer­i­can comedians—even those like Steve Mar­tin, Robin Williams, Jim Car­rey, and Eddie Mur­phy, who were clear­ly influ­enced by his man­ic humor—were often unwill­ing to make too much of the debt. But look­ing back at his 1950s dada zani­ness and at films like The Nut­ty Pro­fes­sor, it’s impos­si­ble to deny his con­tri­bu­tions to 20th cen­tu­ry com­e­dy and even a cer­tain brand of absur­dist 21st cen­tu­ry humor.

Relat­ed Con­tent:

Hear 30 of the Great­est Standup Com­e­dy Albums: A Playlist Cho­sen by Open Cul­ture Read­ers

Chris Rock Cre­ates a List of His 13 Favorite Standup Com­e­dy Spe­cials

Bill Hicks’ 12 Prin­ci­ples of Com­e­dy

Josh Jones is a writer and musi­cian based in Durham, NC. Fol­low him at @jdmagness