Anna Howard Shaw Day

TGS with Tracy Jordan head writer Liz Lemon is due for a root canal. To avoid feeling lonely on Valentine's Day, she schedules her surgery for that day, but soon realizes she will need someone to escort her home from the dentist's office due to the aftereffects of anesthesia. She asks her colleagues at the 30 Rock building for a ride home, but all of them have Valentine's Day plans and cannot help. When Liz calls the dentist's office to say she does not have anyone to pick her up, the receptionist (Shinnerrie Jackson) informs her that after her procedure she can only leave alone if she signs a liability waiver. Liz initially intends to sign the document, but is dissuaded at a party by musician Jon Bon Jovi, and instead decides to claim to the receptionist that she has a ride home after all.

Jack Donaghy, who is Vice President of East Coast Television and Microwave Oven Programming for General Electric, makes an appearance on the fictional CNBC show The Hot Box. During the appearance, Jack interacts with the show's host, Avery Jessup (Elizabeth Banks), with the two flirting during the broadcast. Avery and Jack share Republican viewpoints, and she asks him out for a drink after the show, which he accepts. They eventually embark on a number of both successful and unsuccessful dates. During one of those dates, Jack invites her to a TGS VIP party he has hastily staged, whereupon he enlists the help of Jon Bon Jovi—at the time NBC's real-life Artist in Residence—to come over and talk to them, in an effort to impress the successful Avery. When Bon Jovi approaches them, though, Jack disregards him due to his own intriguing conversation with Avery, which impresses her even more. After the TGS party, the two go back to Jack's apartment and end up sleeping together.

Elsewhere Jenna begins to worry that her stalker, Maynard Roger Hoynes (Horatio Sanz), has lost interest in her. Jenna tracks down Maynard and her suspicions are confirmed, after he tells her that his therapist encouraged him to stop his obsession with her and move forward. Later, in the 30 Rock building, NBC page Kenneth Parcell (Jack McBrayer) finds Jenna upset in her dressing room. She tells him why she is in that state and shows him letters that Maynard sent to her in the past. Kenneth, however, is confused as to why Jenna misses her stalker, leading her to reveal that Maynard has been the longest relationship she has ever had. The next day, Jenna enters her dressing room and sees that her picture is inscribed with the words "I want to eat your boogers." Jenna is touched to find that Kenneth is responsible for the graffito, and thanks him for his thoughtfulness.

On Valentine's Day, Liz goes to her dentist appointment and tells the receptionist that she did not sign the waiver. After her surgery, Liz reassures the dental staff that the anesthesia is having no effect on her and can take herself home. In the lobby, Liz sees her former boyfriends Drew Baird (Jon Hamm), Dennis Duffy (Dean Winters), and Floyd DeBarber (Jason Sudeikis), and is moved that they came back so that she not be alone on Valentine's Day. Liz is hallucinating, however, and the people she sees as Drew, Dennis, and Floyd are actually the three Jamaican women who are dental assistants at the oral surgeon's office. One of them calls Jack, Liz's boss, asking if he could come pick up Liz and take her home. Jack had just spent the night with Avery, who thinks that the phone call was made up by Jack as an excuse to end the date, but when he invites her to come along, she is impressed by his kindness to Liz.

"Anna Howard Shaw Day" was written by 30 Rock supervising producer Matt Hubbard and directed by Ken Whittingham. This episode was Hubbard's ninth writing credit,^[1] and the second episode for Whittingham who had directed the March 12, 2009, season three episode "The Funcooker".^[2] "Anna Howard Shaw Day" originally aired in the United States on February 11, 2010, on NBC as the thirteenth episode of the show's fourth season and the 71st overall episode of the series.^[3] This episode was filmed on December 9, 2009,^[4] and January 27, 2010.^[5]

In December 2009, it was confirmed that actress Elizabeth Banks would guest star on the show, and in this episode, she played right-wing CNBC anchor Avery Jessup, and love interest to Alec Baldwin's Jack Donaghy.^[6] In an interview with Entertainment Weekly's Michael Ausiello, Banks revealed that she approached the show's staff about making an appearance on the show. "I definitely put feelers out, like, 'I would love to be on your show.' And they did it. They made it happen! I'm a huge fan, so this is a dream come true."^[7] She said that on her first day on set she "begged" producers if she could use a teleprompter—in which she is first introduced in the episode on the set of her show The Hot Box, with her interviewing Jack and another guest (Douglas Rees)—so that she could deliver her lines quickly, explaining that her fast delivery would help "sell" the comedy and her 30 Rock character. They agreed to it, though, a problem ensued when they could not figure the prompter out, which resulted in Banks "throwing fastballs at [Baldwin] and him battling them back as fast as possible and hoping they could cut it together faster than we were doing it."^[8] Banks revealed to Ausiello that she had no intention on becoming a series regular, explaining that she has been having "too much fun" making movies to commit to a television show full-time.^[7]

In October 2009, it was reported that musician Jon Bon Jovi would serve as the first artist in NBC's brand new "artist in residence" program.^[9] In a November 25, 2009, appearance on NBC's The Today Show, Jon Bon Jovi explained that his band (Bon Jovi) had released a new album, The Circle, and that for two months the group would be making appearances on a wide range of NBC broadcast and cable channels to promote it.^[10] On 30 Rock, Jon Bon Jovi played himself and his title as artist in residence was referenced, in which he appears as a contestant on the Bravo cooking reality television series Top Chef, and is later shown strumming the NBC Nightly News theme.^[3]

Actors Jon Hamm, Jason Sudeikis, and Dean Winters reprised their roles, respectively, as Drew Baird, Floyd DeBarber, and Dennis Duffy; former boyfriends of Liz Lemon (Fey).^[11] In the final scene of "Anna Howard Shaw Day", in which she is still under the after effects of anesthesia, Liz "sees" Drew, Floyd, and Dennis speak in Jamaican accents, however, the three men are really three Jamaican dental assistants.^[3] In regards to the accent, Hamm said in an interview "That was given to me literally the day before we shot it. They were like, 'We wrote some more stuff, so we'll see you tomorrow.' I was like, 'Okay, how much more can it be? Oh great, it's a completely different take, awesome.'"^[12]

Comedic actor Jason Sudeikis, who appeared in this episode as Floyd DeBarber, was at the time a main cast member of Saturday Night Live (SNL). Additionally in this episode, Horatio Sanz, who played Maynard Roger Hoynes—Jenna Maroney's stalker—has also appeared in the main cast of SNL.^[13] Fey was the head writer on SNL from 1999 until 2006.^[14]

The name of "Anna Howard Shaw Day" is based on Liz's hatred of Valentine's Day, for which she substitutes "Anna Howard Shaw Day", a fictional holiday celebrating the real February 14 birthday of Woman's Civil Rights leader Anna Howard Shaw.^[3][15] Liz tells Jack that she does not watch CNBC, a business news channel, but that she gets all her money advice from a fictitious cartoon character, Foxy Moneybags, on PBS.^[16][17] While confronting him, Jenna asks Maynard if the dog who gives him his orders has died, a reference to the Son of Sam killer allegedly being commanded to kill by a neighbor's possessed dog. As he does not stalk her anymore, Jenna asks Maynard if he is stalking "one of those kids from Glee", the latter being a Fox program that focuses on a high school show choir.^[3] During his appearance on The Hot Box, Avery asks Jack what his favorite movie is with him responding that it is a tie with The Fountainhead (1949) and Uncle Buck (1989).^[3] During her hallucination, in which she sees Drew, Dennis, and Floyd, Liz confesses to Dennis that watching the period drama The Color Purple with him drunk "was one of the funnest nights of my life."^[18]

The character Astronaut Mike Dexter was referenced in this episode, in which Liz tells the dental receptionist that she did not sign the liability waiver as her "boyfriend" Mike Dexter would come and take her home.^[3][19] Liz considers the character to be her imaginary perfect husband.^[20] The character was first introduced in "Sun Tea", in which "Dot Com" Slattery (Kevin Brown) pretended to be Mike Dexter, Liz's "crazy black boyfriend", after she planned to get her roommate out of his apartment with Dot Com's help, but her plan backfired.^[20] In "Dealbreakers Talk Show", Liz's imagination of Mike Dexter was played by actor John Anderson,^[21] in a scene where Liz fantasizes about what her life would be like following the success of her talk show, and is then notified by Mike Dexter that he has to go back to outer space.^[22] Astronaut Mike Dexter would be mentioned further in the season, but near its end Liz decides her infatuation with him is pathetic and "breaks up" with him in a dream; along with her S4 finale meeting of a pilot played by Matt Damon and her brusque breakup with and dismissal of an annoying anti-love interest played by Michael Sheen; this sets the stage for Liz Lemon to be portrayed as much less of a loser from Season 5 through the series finale.