Caricatures (I did an enormous number of these in my teens, including all the U.S. presidents to date. Caricaturing teachers was a great way to make friends.)

A couple of high school teachers (names  long forgotten):

Driver Ed Teacher as rhino

Brainy English Teacher

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A selection of U.S. Presidents:

John Adams

James Madison

Martin van Buren

John Tyler

James K. Polk

Franklin Pierce

Abraham Lincoln

Grover Cleveland

Theodore Roosevelt

William Howard Taft

Woodrow Wilson

Calvin Coolidge

Harry Truman

Dwight Eisenhower

Richard Nixon (he was such a gift to cartoonists! I was in high school during Watergate.)

Nixon

Richard Nixon - Henry Kissinger

Nixon - Novus Ordo Scelerum (A New Order of Crimes)
(rather clever if you know Latin...)

Gerald Ford (also fun to draw)

Ford (he was intellectually underrated at the time)

Gerald Ford - Turtle on Wheels
(to the best of my recollection, the point was:
after a slow start Ford was picking up steam.)

"What Shall We Throw in Next?"

Gerald Ford and Henry Kissinger
(Ford supposedly considered sacking Kissinger)

Jimmy Carter

Leonid Brezhnev (actually, not a U.S President, but also fun to draw)

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Some musicians:

Igor Stravinsky

Charles Mingus

Paul Simon

Art Garfunkel

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Harvard Faculty of the 1970s:

Dean Henry Rosovsky

John Kenneth Galbraith

James Watson

Juan Marichal

Harvard Old Testament Faculty Roasting a Graduate Student

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Family portraits:

Brother Jim Propp as Alchemist

Father Ted Propp

Myself

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Artists and artworks:

La Gioconda?

David

Moses

Auguste Renoir

Vincent Van Gogh

Vincent Van Gogh

Marc Chagall

Pablo Picasso

Pablo Picasso

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Writers:

William Shakespeare

Samuel Beckett

Samuel Beckett

Woody Allen

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In a class by himself:

Albert Einstein

(I apologize that all these are men; I have drawn women too, but the fact is that, until recently, most famous people have been male, except for beautiful actresses, who are inherently difficult to caricature--unless you are Al Hirschfeld!)

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As is tradition, I learned to caricature by copying "masters," primarily the celebrated David Levine

William F. Buckley after David Levine

(this is a naked forgery, down to the signature)

and the more obscure Kai Heinonen, who signed his work "KAI."

Governor and Vice President Nelson Rockefeller after KAI

Sammy Davis Jr. after KAI

Gov. George Wallace (I cannot remember whether this is by me, or another Heinonen copy)

I was once working in a museum in front of a portrait of Martin Luther, and a kid, maybe 12, came up to me and said, awestruck, "Are you KAI?"  Though this really isn't up to Heinonen's level, the incident proved that I had reached a certain proficiency in the craft of forgery.

Martin Luther