When Hugh Jackman puts his swarthy charm on full display as host of this year's Oscars, his legacy (and likelihood of being hired again) will be cemented by the time the first-timer's intro bit has wrapped.

Hosting the Academy Awards is Hollywood's toughest gig, and on the occasion of Jackman's maiden voyage, we take a look back at the superstars and the stinkers of movies' biggest night -- which happens to be one of the biggest TV events of the year.

See our photo gallery of previous Oscars hosts

The Best

Bob Hope: Hosted 18 times between 1939 and 1977

Was there anyone better at good-clean-fun that was actually, well, funny? Hope's breezy Everyman appeal was a natural fit with the early years of the Oscars' telecast, which was often stilted, slow and boring. He was a master of off-the-cuff, friendly humor that today would probably seem goody-goody, but back in the day, Hope was perfect: a true master of ceremony.

Johnny Carson: Hosted five times between 1978 and 1983

Jackman cited Carson as his Oscar-host inspiration, and for good reason. The same approach that made Carson the king of late-night (impish charm, razor-sharp timing, perpetuating running jokes throughout the show) made him Oscar's ideal host. "I see a lot of new faces, especially on the old faces," Carson offered at the 1979 show, an observation met with laughter and claps from the very people he was lampooning. Many hosts have since attempted this routine, but only Carson had the wit and respect of his audience to pull it off.

Billy Crystal: Hosted eight times between 1989 and 2003

Oh, I do miss Crystal, who single-handedly made the Oscars telecast must-see TV throughout 1990s. From his countless clever video montages to his rapport with guests (the Jack Palance bit in the late 1980s with the famous one-handed push-up was a highlight), sunny attitude (he's that rare happy comedian), and overall lacking of musical talent during the song-and-dance numbers turned what in previous years would have been Vegas cheese into an elevated form of wicked-smart slapstick. Crystal was king.

See the 2009 Oscar nominees

Whoopi Goldberg: 1993, 1995, 1998, 2001

Looking back, I'm surprised Goldberg hosted as many times as she did, what with our love affair with Crystal in full swing around the same time. But the comedienne (and good pal of Crystal) consistently held her own as Oscar's first female, first African-American, and first Oscar-winner to ever host on her own. She wisely never shied away from looking silly -- emerging onstage dressed in full Queen Elizabeth regalia, complete with a powdered face -- and, despite her tendency toward bluer comedy as a stand-up comedienne, Goldberg kept it pretty clean and classy, which is exactly what she was paid to do.

Jon Stewart: 2005, 2007

Critics were hard on Stewart after his first stint in 2005, which is probably why last year's appearance was sharper and funnier. His Hollywood-outsider persona was a perfect fit for the Oscars (he frequently makes fun of his lack of acting ability on The Daily Show) and the fact that he hosted during the campaign season didn't hurt: "Normally when you see a black man or a woman president, an asteroid is about to hit the Statue of Liberty," said Stewart last year. And, he wasn't all sarcasm, either: the best part of last year's show was when Stewart brought songwriter Marketa Irglova (Once) back onstage so she could finish her speech. For me, Stewart struck all the right chords.

See our Best and Worst Oscars red carpet looks

The Worst

Jerry Lewis: 1955, 1956, 1958

I feel kinda bad for lambasting Lewis, especially when the irascible comic is set to receive a lifetime achievement Oscar at this year's ceremony. The finale to the 1958 telecast was a small disaster: The show ended with Gigi winning Best Picture, yet the there was still 20 minutes of airtime left to fill. Solution? Lewis led the audience in a disastrous rendition of “There’s No Business Like Show Business” -- during which Lewis madly shouted, “Keep singing!” -- and then attempted to ad-lib the rest of the show. No, it wasn't totally his fault, but the show was a dark spot nonetheless in the annals of Oscar hosts.

Chevy Chase: 1987

I've always loved Chevy Chase (Fletch is my favorite comedy of all time), but his second attempt at Oscar-host glory (he'd co-hosted the year before) just didn't agree with the SNL alum. His intro about "Hollywood phones" was awkward and rant-like (bitter, party of one?) and a string of jabs at critics and the year's nominees came across as immature and a little sad. This was one of many cases where a superior wit and acerbic sensibility (see Letterman below) failed profoundly.

David Letterman: 1994

Who could forget the infamous “Oprah, Uma” routine? Sadly, it's the only thing remotely noteworthy or memorable about Letterman's one and only shot at hosting. His propensity toward self-deprecation and mockery is a slam-dunk on The Late Show, but was a terrible fit for the Oscars. You could feel some of the dead silences between jokes. Eesh. Thankfully, Letterman has no problem poking fun at his failures, and appeared in the 1995 telecast making fun of his pathetic performance. You gotta love him for that.

Chris Rock: 2004

Carson proved that ridiculing Hollywood at the Oscars is an art form: you don't want to actually piss people off. Rock, in true caustic form, did just that when he got personal during his one and only hosting gig, making fun of Jude Law, saying that some of the nominated films "sucked," and featuring a video montage wherein he interviewed average moviegoers who hadn't a clue which movies were even nominated that year. The funniest part of the whole thing was that Rock had actually toned down his routine for the occasion. Yikes.

Ellen DeGeneres: 2006

It pains me a little to include my fave funny lady in this list, but her "I'm goofy! Watch me dance!" shtick simply didn't work at the Oscars. Her audience interactions were awkward (here I'm recalling a bewildered-looking Clint Eastwood and Marty Scorsese) but mostly I think DeGeneres was just too nicey-nice and too close of friends with folks in the audience to deliver the wry wit needed to keep the show mildly edgy. Best to stick with daytime, toots.

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