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=== 1986β1999: Oscar host and leading man status === Due to the success of Crystal's standup and ''[[Saturday Night Live|SNL]]'' career, in 1985, he released an album of his stand-up material titled ''Mahvelous!''. The title track ''You Look Marvelous'', written by Crystal and [[Paul Shaffer]], had an accompanying music video that debuted on [[MTV]].<ref>{{Cite magazine|url=https://www.rollingstone.com/culture/culture-features/billy-crystals-winning-season-126456/|title=Billy Crystal's Winning Season|first1=Debby|last1=Bull|magazine=[[Rolling Stone]]|date=October 24, 1985}}</ref> Both the song and video features Crystal in character as his [[SNL]] persona of talk show host [[Fernando Lamas]]. The video features Lamas cruising around in what was at the time the world's longest stretch limousine, built by custom-coach designer and builder Vini Bergeman,<ref>{{Cite web|url=https://www.thedrive.com/news/32769/the-larger-than-life-tale-of-vini-big-daddy-bergeman-the-limo-king-of-los-angeles|title=The Larger-Than-Life Tale of Vini 'Big Daddy' Bergeman, the Limo King of Los Angeles|first=Roger|last=Garbow|website=The Drive|date=March 27, 2020 }}</ref> surrounded by models in bikinis. The single peaked at No. 58 on the [[Billboard Hot 100|''Billboard'' Hot 100]] in the US and No. 17 in Canada. The album was nominated for a [[Grammy Awards|Grammy]] Award for Best Comedy Recording at the 1986 Grammy Awards.<ref>{{Cite web|url=https://www.discogs.com/Billy-Crystal-You-Look-Marvelous/release/126683|title=Billy Crystal β You Look Marvelous|website=Discogs|year=1985 }}</ref><ref name="grammy.com">{{Cite web|url=https://www.grammy.com/grammys/artists/billy-crystal|title=Billy Crystal|date=November 19, 2019|website=grammy.com}}</ref> He later starred in the action comedy ''[[Running Scared (1986 film)|Running Scared]]'' (1986) opposite [[Gregory Hines]]. Film critic of the ''[[Chicago Sun-Times]]'' [[Roger Ebert]] praised the two for their on-screen chemistry writing, "But Crystal and Hines...don't need a plot because they have so much good dialogue and such a great screen relationship."<ref>{{cite web|url= https://www.rogerebert.com/reviews/running-scared-1986-1986|title= Running Scared (1986) movie review|website= Rogerebert.com|accessdate= January 3, 2023}}</ref> During this time, Crystal hosted the [[Academy Awards]] broadcast a total of nine times, from [[62nd Academy Awards|1990]], [[63rd Academy Awards|1991]], [[64th Academy Awards|1992]], [[65th Academy Awards|1993]], [[69th Academy Awards|1997]], [[70th Academy Awards|1998]], [[72nd Academy Awards|2000]], [[76th Academy Awards|2004]] and [[84th Academy Awards|2012]]. His hosting was critically praised, resulting in two [[Primetime Emmy Award]] wins for hosting and writing the [[63rd Academy Awards]] and an Emmy win for writing the [[64th Academy Awards]]. ''[[San Francisco Chronicle]]'' columnist John Carman raved about Crystal's performance for the [[70th Academy Awards]] writing, "It was the best Oscar show in two decades...Crystal was back in razor form."<ref>{{cite news|last=Carman |first=John |title=Oscar Polishes Up His Image / Crystal clearly a winner for best show in decades |url=http://www.sfgate.com/entertainment/article/Oscar-Polishes-Up-His-Image-Crystal-clearly-a-3011121.php |access-date=January 23, 2014 |work=[[San Francisco Chronicle]] |publisher=[[Hearst Corporation]] |date=March 24, 1998 |url-status=live |archive-url=https://web.archive.org/web/20140202225702/http://www.sfgate.com/entertainment/article/Oscar-Polishes-Up-His-Image-Crystal-clearly-a-3011121.php |archive-date=February 2, 2014}}</ref> ''[[The Seattle Times]]'' television editor Kay McFadden praised Crystal commenting that "he possesses nearly impeccable timing and judgment."<ref>{{cite news|last=McFadden |first=Kay |title=Ceremony Shapes Up As A Night To Remember |url=https://archive.seattletimes.com/archive/19980324/2741394/ceremony-shapes-up-as-a-night-to-remember |access-date=January 23, 2014 |work=[[The Seattle Times]] |publisher=[[The Seattle Times Company]] |date=March 24, 1998 |url-status=live |archive-url=https://web.archive.org/web/20140201200513/http://community.seattletimes.nwsource.com/archive/?date=19980324&slug=2741394 |archive-date=February 1, 2014}}</ref> Crystal reunited with director Rob Reiner in ''[[The Princess Bride (film)|The Princess Bride]]'' (1987), in a comedic supporting role as "Miracle Max." Reiner got Crystal to accept the part by saying, "How would you like to play Mel Brooks?" Reiner also allowed Crystal to ad-lib, and his parting shot, "Have fun storming the castle!" is a frequently quoted line. Critic [[Roger Ebert]] described Crystal as a highlight of the film writing "the funniest sequences in the film stars Billy Crystal and Carol Kane, both unrecogizable behind makeup, as an ancient wizard and crone who specialize in bringing the dead back to life."<ref>{{cite web|url= https://www.rogerebert.com/reviews/the-princess-bride-1987|title= The Princess Bride|website= Rogerebert.com|accessdate= June 22, 2023}}</ref> Reiner directed Crystal for a third time in the romantic comedy ''[[When Harry Met Sally...]]'' (1989). Crystal starred alongside [[Meg Ryan]], [[Bruno Kirby]] and [[Carrie Fisher]] in a script written by [[Nora Ephron]]. ''[[The Hollywood Reporter]]'' praised the film and Crystal's performance writing, "Crystal's lustrous, deeply-shaded performance is certain to win him legions of new fans; indeed, his prowess as a comic reaches its deepest human dimension here."<ref>{{cite web|url= https://www.hollywoodreporter.com/news/general-news/harry-met-sally-1989-review-959579/|title= 'When Harry Met Sally': THR's 1989 Review|website= [[The Hollywood Reporter]]|date= December 28, 2016|accessdate= June 22, 2023}}</ref> Crystal was nominated for the [[Golden Globe Award for Best Actor β Motion Picture Musical or Comedy]] losing to [[Morgan Freeman]] in ''[[Driving Miss Daisy]]'' (1989). The film has since become an iconic classic for the genre and is Crystal's most celebrated film. In 2019, the [[BBC]] named the film the greatest romantic comedy of all time.<ref>{{cite web|url= https://www.bbc.com/culture/article/20190705-why-when-harry-met-sally-is-the-greatest-romcom-of-all-time|title= Why When Harry met Sally is the greatest romcom of all time|website= [[BBC]]|date= July 12, 2019|accessdate= June 22, 2023}}</ref> In 1991, Crystal created and produced the HBO six-part comedy miniseries ''[[Sessions (TV miniseries)|Sessions]]'' starring [[Michael McKean]] and [[Elliott Gould]]. The ''[[Los Angeles Times]]'' praised the project describing it as "swankily written, elegantly staged and perfectly cast."<ref>{{cite web|url= https://www.latimes.com/archives/la-xpm-1991-10-05-ca-3035-story.html|title= TV Review : Comedy on a Couch in Billy Crystal's 'Sessions'|website= [[Los Angeles Times]]|date= October 5, 1991|accessdate= June 22, 2023}}</ref> Crystal then starred in the award-winning buddy comedy ''[[City Slickers]]'' (1991), which proved very successful both commercially and critically and for which Crystal was nominated for his second [[Golden Globe Awards|Golden Globe]]. The film was followed by a sequel, which was less successful. The name of his company is Face Productions.<ref>{{Cite web|date=November 12, 2013|title=Billy Crystal|url=https://variety.com/exec/billy-crystal/|access-date=October 15, 2020|website=Variety|language=en}}</ref> ''[[Entertainment Weekly]]'' praised Crystal's performance writing, "It's also the first movie ever to do the talented Billy Crystal justice...he's far more pleasureful to watch in this sort of dramatic-comedy role than, say, Robin Williams, because his comfy, urban-shlemiel personality helps ground the jokes."<ref>{{cite magazine|url= https://ew.com/article/1991/06/14/city-slickers-3/|title= City Slickers|magazine= [[Entertainment Weekly]]|accessdate= June 22, 2023}}</ref> Following the significant success of these films, Crystal wrote, directed, and starred in ''[[Mr. Saturday Night]]'' (1992) and ''[[Forget Paris]]'' (1995). In the former, Crystal played a serious role in aging makeup, as an egotistical comedian who reflects back on his career. In 1992, Crystal narrated ''[[Dr. Seuss]] Video Classics: [[Horton Hatches the Egg]]''. He was originally asked to voice [[Buzz Lightyear]] in ''[[Toy Story]]'' (1995) but turned it down, a decision he later regretted due to the popularity of the series.<ref name="actors" /> Crystal later films include a supporting roles in [[Kenneth Branagh]]'s [[William Shakespeare]] epic ''[[Hamlet (1996 film)|Hamlet]]'' (1996), and [[Woody Allen]]'s critically acclaimed comedy ensemble film ''[[Deconstructing Harry]]'' (1997). Crystal had starred opposite [[Robin Williams]] in ''[[Father's Day (1997 film)|Father's Day]]'' (1997) and had success alongside [[Robert De Niro]] in [[Harold Ramis]]' mobster comedy ''[[Analyze This]]'' (1999). In 1996, Crystal was the guest star of the third episode of ''[[Muppets Tonight]]'' and hosted three [[Grammy Award]]s Telecasts: the [[29th Annual Grammy Awards|29th Grammys]]; the [[30th Annual Grammy Awards|30th Grammys]]; and the [[31st Annual Grammy Awards|31st Grammys]]. Crystal was a guest on the first and the last episode of ''[[The Tonight Show with Jay Leno]],'' which concluded February 6, 2014, after 22 seasons on the air.<ref>{{cite web | url = http://www.nbc.com/the-tonight-show/video/thursday-february-6-2014/n45954 | publisher = The Tonight Show with Jay Leno | title = Season 22: Episode 77 | access-date = February 8, 2014 | archive-url = https://web.archive.org/web/20140208002824/http://www.nbc.com/the-tonight-show/video/thursday-february-6-2014/n45954 | archive-date = February 8, 2014 | url-status=dead }}</ref>
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