When we ranked Jack Donaghy’s girlfriends, we were essentially limited to five contenders so it didn’t make much sense to call it a top five. Where Liz Lemon’s love life is concerned, we can reasonably cast a wider net.
Whereas Jack’s love life tends to be defined by season-long ladyfriends, Liz has many more one-offs that we think deserve to be considered for a post such as this. So, our only real requirement here is that she had some kind of romantic involvement with the person during the course of the show, even if only for a single episode. Sorry, Conan O’Brien, but you and Liz were an item before the timeline of the show begins! Okay, let’s get to it.
5. Gretchen Thomas
This might be a bit of a cheat because Gretchen (Stephanie March) and Liz weren’t technically romantically involved. Also she’s not male, and the title of the post says boyfriends. But! The brilliant plastics engineer/lesbian takes the fifth spot on our list because after she and Liz were set up in “Blind Date,” they continued a relationship that resembled something more than a traditional friendship. Their friendship ultimately had to end because Thomas’s feelings for Liz became too strong, and she knew Liz did not feel the same way. It was a shame really. The two got on so well that even Liz’s coworkers wanted the them to make it work somehow. We did too!
4. Jamie / Danny Baker
Another cheat! But hear me out: Liz frequently takes on a more passive (or lazy even–I don’t necessarily mean submissive) role in a relationship so it was a treat to see her play the take-charge alpha in these two scenarios — even if she needed Jack to coach her a little — and that’s why we’ve grouped them together.
In “Cougars,” Liz plays the mature, financially solvent career woman to Jamie’s barely legal, broke coffee gofer. Both Liz and Jamie (Val Emmich) lie about their age, and when the truth is revealed, Liz blurts out: “This just went from a senior dating a freshman to Mary Kay Letourneau and Vili Fualaau.” Matters only worsen when Jamie’s Oedipal complex comes to light. “Shut it down.” Their union was doomed from the start, but this is a fling we’re happy Liz had.
In “Black Light Attack,” Jack initially says that Liz should be “taking her reward” from younger subordinates, but when she chooses Danny (Cheyenne Jackson) to be her “scrump-nugget,” Jack objects because he wants Danny to be his bro. (Side note: this isn’t the first time Liz and Jack have competed for a man’s attention.) We love the authority Liz wields over Danny, and their CHiPs roleplaying is legendary.
3. Carol Burnett
Some of Liz’s longterm loves have left us cold, or at least the level of comedy becomes uneven or decreases the longer she’s with some of them. Carol is the exception to the rule. Played by Matt Damon, Carol brings the lulz in his interactions both with Liz and with the TGS staff, but the major reason Carol placed on this list is the episode “Double-Edged Sword.” In it, Liz and Carol’s relationship implodes spectacularly while the two are trapped on a grounded plane. Their fight reaches its epic tipping point when Carol literally points a gun at Liz and shouts, “I will waste you!” Dang, 30 Rock, you just went all the way there. It would be scary if it wasn’t so absurdly funny.
2. Wesley Snipes
Michael Sheen guest stars in a handful of season 3 episodes as the Brit with the familiar name (“You’d pick the pale Englishman every time!”). In “Future Husband,” Liz finds the “future husband” number saved in her phone and learns she bonded with Wesley in the oral surgery recovery room. After the two connect and try to understand why they were so enamored with each other, they just do not get along, and the interplay between Sheen and Fey is hilarious. They discover their connection had everything to do with anesthesia and nothing to do with true love. Wesley suggests the two are actually “settling soul mates,” a concept Liz initially finds too depressing to accept. Liz eventually gives the settling soul mate thing another try when she’s desperate for a date to a wedding, but she subsequently meets Carol and sets off on a different course.
1. Dennis Duffy
“Hey, dummy.” Could number one be anybody else but Dennis Duffy? Dennis, Beeper King and Subway Hero. Dennis, coffee machine entrepreneur and (exonerated) Dateline Predator. The vaguely sexist, racist, homophobic bridge and tunnel loser is played with jerky charisma by Oz star Dean Winters. Dennis is yang to Liz’s yin, right down to his complementary alliterative name. Although we know Dennis is no good for Liz (or anyone, for that matter) in the longterm, he remains an extremely enjoyable character, a foil for Liz Lemon and consistent source of big laughs.