Prior to the start of the season, a large number of cast changes occurred. Longtime cast members Fred Armisen, Bill Hader and Jason Sudeikis all departed the show. In addition, featured player Tim Robinson left the cast to focus on his new duties in the writing staff, becoming the first performer to join the writing staff after being a cast member without initially being hired as a writer. Aidy Bryant, Kate McKinnon and Cecily Strong were all promoted to repertory status. The show hired six new featured players, including SNL writer Mike O'Brien who was upgraded into the cast, as well as new hires Beck Bennett and Kyle Mooney of the sketch comedy groupGood Neighbor, John Milhiser of the sketch group Serious Lunch, comedian Noël Wells, and stand-up comedian Brooks Wheelan. Mooney auditioned for the show in 2012 for the previous season. O'Brien had written for the show since 2009 and was the first writer to be upgraded into the cast since Jason Sudeikis in 2005. Bennett and Mooney's fellow Good Neighbor troupe member Dave McCary was also hired to direct Bennett and Mooney's digital shorts. On May 12, 2013, NBC announced that Weekend Update anchor Seth Meyers would be the new host of Late Night in 2014 succeeding Jimmy Fallon as Fallon was taking over as the new host of The Tonight Show. Meyers remained Weekend Update anchor up until his departure from the show on February 1, 2014. Cecily Strong was brought up to co-anchor with Meyers. Colin Jost, a writer for the show, joined the cast on March 1, 2014, as a featured player and as Meyers' successor on Weekend Update. This is the third time a featured player was also a Weekend Update anchor. The first two were Tina Fey and Brian Doyle-Murray. Strong was replaced the next year by former writer and Daily Show correspondent Michael Che. During the season, the show came under criticism from critics for not including at least one black female cast member, a topic that was addressed on the November 2, 2013, show hosted by Kerry Washington. As a result, Lorne Michaels announced that the show would be holding auditions for a black female cast member, expected to join the show in January as a new featured player. On January 6, 2014, it was announced that UCB-NY performer Sasheer Zamata would be joining the cast as a new featured player. She made her first appearance on January 18, 2014. The addition of eight new cast members is the greatest since the 1995–96 season, during which nine cast members were added, making it the largest cast overhaul in eighteen years. The total of 17 cast members was an SNL record, and some critics argued that the large cast contributed to how uneven the season was overall. This would be the final season for Nasim Pedrad, who had been a cast member since 2009. She announced her departure from the show in June 2014 in order to work on the Lorne Michaels-produced show, Mulaney. Additionally, John Milhiser, Noël Wells, and Brooks Wheelan were fired from the show after one season. Also, Mike O'Brien left to return to the writer's room. This would also be the final season for longtime announcer Don Pardo, who died on August 18, 2014, at the age of 96.
For the first half of the season, Seth Meyers, Colin Jost and Rob Klein were co-head writers. After Meyers' departure, Bryan Tucker replaced him as a co-head writer. Prior to the start of the season, three new writers were hired:
Mikey Day, a member of The Groundlings and cast member on MTV's Wild 'N Out
Michael Che, a standup comic who had guest written for five episodes in season 38, was hired as a full-time writer.
Additionally, Tim Robinson was moved to the writing staff after one year as a featured player on the show. In December, Chicago Second City alum Katie Rich joined the writing staff. In January, comedians LaKendra Tookes and Leslie Jones were added to the writing staff. Both were part of the December casting call for a black female cast member. This was Seth Meyers' final season as writer. Michael Che initially departed following this season to join The Daily Show as a correspondent, but returned for the start of the next season to co-anchor Weekend Update alongside Jost. This was also the final season for longtime writers Alex Baze, Marika Sawyer and John Solomon, as well as the only season for LaKendra Tookes.
