A Grander World: A Collaborative TL

January 12, 1997: The Jacksonville Jaguars stun the world by defeating the New England Patriots to advance to the Super Bowl in just their 2nd season. Meanwhile, their fellow expansion team, the Carolina Panthers, defeat the Green Bay Packers to advance to the Super Bowl. This makes the quickest time an expansion team has advanced to the Super Bowl.
We'll to @Inferno60, change, since it covered mostly post-1999 stuff, to friends @kaijudirector , @SomeGuyOnline and @Marco Incognito .
January 31, 1999: The Super Bowl made history when the Denver Broncos beat the Atlanta Falcons. Family Guy also premiered on Fox.
September 28, 1999: A half-hour edited version of Ally McBeal, Ally made its debut on FOX.

November 1, 1999: The half-hour edited version of Ally became a success, it received a full episode order.

May 1, 2000
: The half-hour Ally was renewed for a second season by FOX.
October 25, 1999: Time of Your Life, a spinoff of Party of Five made its debut on FOX.

November 5, 1999: Sinclair Broadcast Group purchases WNAB for $24.5 million.
January 13, 1999: 60 Minutes II will premiere on CBS.

October 25, 2007: The final negotiations between the WGA and AMPTP begin, and talks succeeded.

To @SomeGuyOnline, any chances that the WGA strike of 2007-08 will not happen TTL, thus as a result, 24 will return on time on January 13, 2008, and did not shorten seasons.
March 16, 2000: The Green Mile wins Best Picture, Best Supporting Actor (for Michael Clarke Duncan), Best Adapted Screenplay, and Best Sound Mixing.
February 11, 1999: LIN Television Corporation outbid Communications Corporation of America for the purchase of WEVV-TV from Ralph Wilson for $32.5 million.

March 2, 1999: James Gilmore, Jr. made an offer that they can't refuse and sell WEHT to Raycom Media for $40 million.

August 3, 1999: Woods Communications made an offer that they can't refuse and forced to sell Fox station WCOV to Raycom Media for $48 million.

March 28, 2006: Raycom Media elects to keep WFIE in Evansville and WSFA in Montgomery and sell WEHT and WCOV, among other stations to Barrington Broadcasting.

February 28, 2013: Sinclair Broadcast Group announces plan to buy all stations from Barrington Broadcasting.

August 9, 2013: Sinclair sells off WSYT to Bristlecone Broadcasting as they prepare to buy WSTM in Syracuse, and also forced to sell KTVX in Salt Lake City to Gray Television, since Sinclair already had KUTV in its portfolio.
To @SomeGuyOnline and @kaijudirector , here's what's happening if the 2007-2008 WGA strike was averted TTL.
April 26, 1999: The Tonight Show with Jay Leno began broadcasting in high definition.

November 5, 2007: A new day and an agreement at the Writers Guild of America and the Alliance of Motion Picture and Television Producers begin, averting the strike.

January 14, 2008: Heroes: Origins made its debut on NBC.
September 24, 1999: Now and Again made its debut on CBS.

May 10, 2000: CBS is voting to keep Now and Again for a second season.

January 13, 2008: The seventh season of 24 made its debut on FOX (OTL it was delayed due to the strike, TTL it was averted).

March 25, 2010: Fox and its executives voted to renew 24 for a tenth network season, in order to continue airing stories in an uninterrupted manner.
March 30, 2000: Wonderland premieres on ABC, and it became a hit.

October 30, 2001: 24 made its debut on FOX, and it became a success.

July 14, 2008: Landmark Media Enterprises announced that they would sell WTVF to Bonten Media Group for more than $200 million.

September 2, 2008: Landmark Media Enterprises announced that they would sell KLAS-TV to New Vision Television for $500 million.

October 1, 2008: News Corporation announced that they would sell WHBQ in Memphis to Bonten Media Group for $150 million.

December 2, 2013: WEHT in Evansville launched a new graphics package, and a new Warner/Chappell Production Music-composed music package to be centralized to all Sinclair stations with news departments.
July 14, 2000: X-Men was released to movie theaters.

November 12, 2001: Battlestar Galactica would survive with Bryan Singer still being attached.

January 4, 2002: FOX is proceeding with a sequel to Battlestar Galactica that was developed by Tom DeSanto and Bryan Singer, the X-Men team. (OTL this was scrapped after the 9/11 attacks, and a reimagining was made instead)

February 4, 2002: German film director Robert Schwentke was enlisted by 20th Century-Fox to direct a sequel to X-Men, X-Men 2.

May 6, 2002: FOX is picking up a sequel series to Battlestar Galactica, to be helmed by Bryan Singer.
February 8, 1999: WGNO's new owners, Media General infused some money into the station, rebranding it to "NewsWatch 26".

March 9, 1999: The Dispatch Broadcast Group announced that they would sell WBNS-AM-FM-TV and WTHR to Clear Channel Communications for $150 million.

March 16, 1999: The Manship family announced that they will planning on to sell WBRZ and KRGV to Spartan Communications for $200 million.

December 8, 1999: Media General announced that they would purchase Spartan Communications, which included newly-acquired stations WKRG, WBRZ and KRGV, for $725 million.
March 21, 2014: Media General and LIN Media announced a $1.6 billion merger agreement.

September 14, 2015: Schurz Communications announced that it would exit broadcasting and sell all stations to Gray Television for $442.5 million.

October 1, 2015: Gray Television announced that it would swap WSBT-TV in South Bend to Media General for KLFY-TV in Lafayette, thus increasing the reach Media General had in Indiana (OTL, Gray swapped WSBT-TV to Sinclair for WLUC-TV in Marquette) and $2 million in cash, and Gray also announced it would swap KAKE to Heartland Media for WKTV and $12.2 million (OTL, Gray swapped KAKE to Lockwood for WBXX and $11.2 million).

January 27, 2016: Nexstar Broadcasting Group announced that it would merge with Media General, this deal included its pending acquisition of WSBT in a swap agreement with Gray Television for KLFY in Lafayette.
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April 4, 2000: Falcone made its debut on CBS, it eventually became a hit show.

August 19, 2005: Emmis Communications announced that they would sell Fox station WVUE-TV to Communications Corporation of America for $125 million.
July 1, 2016: The Divergent Series: Allegiant was released to theaters and it became a hit (here TTL it was delayed from its original March release date to avoid inteference with Disney's animated hit Zootopia).