Letterman: Drew Barrymore Flashes the World
In 1995, most people still thought of Drew Barrymore as the cute little girl from "E.T." This "revealing" interview proved once and for all that she was all grown up.
Leno: Hugh Grant Interview
After being arrested for lewd conduct with prostitute Divine Brown in 1995, Hugh Grant kept his previously arranged commitment to appearing on "The Tonight Show." It was his first public appearance since the incident, and Leno created one of the most memorable events on talk show history with his first question: "What the hell were you thinking?" The actor stammered an adorable response, and all was forgiven.
Letterman: Dave Brings Lindsay Lohan to Tears
In a touching display of rarely seen humanity from Dave, in this clip he makes Lindsay Lohan cry out of happiness. She had been a frequent target of his barbs.
Leno: Pumpcast News
This clip from "The Tonight Show," from a relatively new segment they call "Pumpcast News," recently went viral on the Internet, getting over 16 million hits. Jay may be on his way out, but this proves the host hasn't stopped giving it his all.
Letterman: Farrah Fawcett Drugged
In 1997, Fawcett appeared on Dave's show drugged out of her mind. The icy host turned what could have been an awkward moment into TV gold.
Leno: Fake Michael Jackson Interview
While we still miss the late, great Michael Jackson, we can't help but crack up at this phony interview Leno conducted sometime in the early '90s.
Letterman: Andy Kaufman Fights Pro Wrestler
This 1982 interview with Andy Kaufman quickly went down in history as one of the most memorable moments on late-night television. While later revealed to be a hoax, at the time audiences were shocked when comic Andy Kaufman got into a nasty verbal and physical altercation with pro wrestler Jerry Lawler.
Leno: Jay Walking
In Jay's most famous reoccurring segment, he asks random strangers simple questions and the results are often hilarious (if not incredibly depressing).
Letterman: Extortion Details
After a jilted lover tried to extort him, Dave decided to fight back the best way he knew how: with a brutally honest confession to committing adultery. Did the admission hurt his career? Hardly. Ratings for the show quickly saw a sharp uptick following the program.
Leno: Jay Does Superbowl Commercial With Dave
While Dave (and Oprah) also appeared in this Superbowl commercial, Leno should get extra credit for nationally poking fun at himself. At the time, he had recently replaced Conan as the host of "The Tonight Show," and the public was calling for Leno's head.
RELATED: Famous People's Doodles Exposed
Intimate moments in the brief life of an iconic actor
13 breathtakingly romantic moments in classic movies
14 photos that reflect the magic of a 50-year marriage
9 indelible quotes from Jefferson Airplane co-founder Paul Kantner
Middle age – with all of its inherent craziness – was made for the movies
11 unlikely but inspiring celebrity friendships