15 Best Guest Stars On How I Met Your Mother

For nine seasons, "How I Met Your Mother" recounts the tale of how Josh Radnor's Ted Mosby eventually meets the mother of his children, Tracy McConnell (Cristin Milioti). Ted isn't alone on his journey; he's accompanied by his core group of friends as they live, work, and find love in New York City. In addition, "How I Met Your Mother" had a revolving door of guest stars who helped make the series one of the best sitcoms of its era.

The CBS show attracted the likes of TV legends like Alan Thicke and Bob Barker, as well as A-list singers like Katy Perry and Jennifer Lopez. The series also featured up-and-comers like Lucy Hale and Lin-Manuel Miranda who were just about to break out into stardom. Whether they appeared for a single episode for a cameo or a multi-episode arc, these guest stars left an impression. From the Blitz to the Captain and everyone in-between, here are the greatest "HIMYM" guest stars.

Prior to arriving in the U.S., Robin Scherbatsky (Cobie Smulders) had a full career as the Canadian teen star Robin Sparkles. Before she began her pop career with the hit single "Let's Go to the Mall" Robin starred on the kids show "Space Teens," which featured Alan Thicke. The "Growing Pains" star acted as a guide to Robin and Jessica Glitter (Nicole Scherzinger) as they solved crimes across the galaxy through math problems.

Thicke appeared five times over the course of "HIMYM." He has a cameo in the Robin Sparkles music video "Sandcastles in the Sand." Thicke was recruited to help break up Robin and Barney Stinson (Neil Patrick Harris) in Season 5's "The Rough Patch." In Season 8, Barney physically confronts Thicke when he's convinced that he was the subject of Robin's turn to grunge "P.S. I Love You"... but the real subject was Paul Shaffer. Although he and Barney exchanged punches over the misunderstanding, Alan Thicke, whose real world counterpart passed away in 2016, attends Barney and Robin's rehearsal dinner in the final season.

In Season 2's "Showdown," Barney gets the chance of a lifetime to appear on the hit game show "The Price is Right." In the lead up, he's completely dedicated to his training. Why? When he was young and asked his mother who his father was, she told him it was Bob Barker. Barney's plan is to win so that he can reunite with his absentee dad and tell him the truth on national television.

When his time on "The Price is Right" arrives, Barney does exceptionally well, impressing Barker and the audience with his accurate price guesses. When he gets the chance to tell the iconic game show host that he's his father, Barney stops himself. Instead, he congratulates Barker for his over three decades of hosting the popular game show. In the end, Barney gifts most of his winnings to Lily (Alyson Hannigan) and Marshall (Jason Segel) for their upcoming wedding. Compared to Barker's role in "Happy Gilmore," this appearance is refreshingly nonviolent.

Pop princess Britney Spears showed off her comedic chops for two episodes of the CBS sitcom. In Season 3's "Ten Sessions" Spears appeared as Abby, a receptionist for Stella (Sarah Chalke), who watches Stella reject Ted's advances. Hoping to impress Stella, Ted is friendly with Abby, and then Abby develops a crush on Ted. As Ted's affections lie elsewhere, Barney ends up swooping in on Abby. After their one-night stand, she sabotages Barney's dates, but the two later conspire to make Ted jealous by acting like an in-love couple in the episode "Everything Must Go."

Spears — who was still one of the biggest pop stars in the world at the time — gave the series a ratings boost and exposed it to a wider audience, which couldn't have hurt its long-term popularity.

Bryan Cranston appeared twice during "HIMYM" Season 2. Here, he played Hammond Druthers, Ted's arrogant boss. Hammond keeps everyone, including Ted, on edge because of his bad attitude. When Lily briefly works at the same firm as an office assistant, she tries to teach Hammond a lesson by hiding his prized baseball in the episode "Aldrin Justice." This only enrages him more, as he threatens to go on a firing spree if his baseball isn't returned.

Later in the season, Ted is the project lead on a new design, making him Hammond's boss. When his attitude doesn't improve, Ted fires Hammond at the worst possible time — in the middle of a heart attack. Hammond survives, and later in Season 9's "Platonish," he reaches out to offer Ted a job at his firm in Chicago. 

A few years after his initial appearance in "HIMYM," Cranston went on to star in the famous AMC crime series "Breaking Bad."

Barney Stinson was the most notorious womanizer in the Big Apple. However, his confidence is shaken after he reunites with Rhonda (Stephanie Faracy), the woman he lost his virginity to, and learns that she wasn't impressed by their experience together. In fact, the only reason Rhonda slept with him was because his brother bribed her. This puts him in a bit of a funk in Season 3's "The Yips," as he strikes out hard while trying to pick up models at the Victoria's Secret Fashion Show afterparty. One of the models he attempts to hit on is none other than the famous model Heidi Klum.

After he fails to seduce her, Klum is witness to Barney's breakdown, as Ted informs her that Barney has the yips. Instead of leaving Barney in his distress, the "Project Runway" host advises him that the only way to get over the yips is to find Rhonda and earn that confidence back for real. Thanks to Klum's advice, Barney finds Rhonda and gets his groove back.

There are only a handful of women immune to Barney's charm. One of those women is Anita, played by the Golden Globe nominated actress and singer Jennifer Lopez. After Barney fails to keep Anita over at his place in Season 5's "Of Course," he discovers that Anita wrote a relationship book that encouraged women to not fall for untrustworthy men and wait 17 dates before consummating the relationship. This puts Barney on a mission to break this boundary of hers... not knowing that Robin and Anita are secretly working together to mess with him.

Lopez's previous sitcom appearance on "Will & Grace" was a cameo. Her "HIMYM" role was thought to have helped put her back on the map amidst some tabloid drama at the time. Lopez as Anita was a welcomed guest actress who briefly beat Barney at his own game, as well as help him realize how insensitive he had been towards Robin.

One of the ongoing mysteries of "HIMYM" was the identity of Barney's dad. In Season 6's "Legendaddy" the long-awaited reveal finally happens. It turns out Barney's father is not the renowned game show host Bob Barker, but a repairman and suburban dad played by John Lithgow. This discovery was made when an old file from the National History Museum listed Jerome as Barney's dad instead of "Uncle Jerry" in Season 6's "Natural History."

Instead of the awesome man Barney had built up in his head, Jerry leads a simple life with his own family in the suburbs. After a disastrous dinner with his family, the two have an emotional confrontation while Barney attempts to steal a basketball hoop. It's rare in "HIMYM" for Barney to show any type of despair like this, and the "3rd Rock from the Sun" star matched Harris well for this moment.

"HIMYM" Thanksgiving episodes are some of the series' best. While the "Slapsgiving" installments are excellent, Season 6's "Blitzgiving" is another worthy chapter thanks to the guest spot of "Lost" star Jorge Garcia. In college, Ted and Marshall were friends with Steve Henry, a man who was cursed with "The Blitz" — something amazing happens every time he leaves an event early.

Thanks to his early departure for his "turturkeykey" preparations, Ted is cursed as The Blitz, freeing Steve for an epic night out with the gang and Ted's nemesis Zoey (Jennifer Morrison). The curse passes briefly to Barney after he takes a separate cab to Zoey's apartment for Thanksgiving. Unfortunately, The Blitz returns back to its original host by the end of the episode in a cruel twist of irony. Too bad Garcia couldn't stick around the sitcom longer since ABC's "Lost" had finished earlier that year.

Early in Season 1 of "HIMYM," fans are introduced to the mystery of the "Sl***y Pumpkin," a woman Ted hit it off with at a rooftop Halloween party. For years, Ted dressed up as a "Hanging Chad" and attended this Halloween party in hopes of reuniting with the promiscuous pumpkin (a nod to Linus waiting for The Great Pumpkin in "It's the Great Pumpkin, Charlie Brown"). In Season 1, this mysterious woman wasn't attached to an actress. It's not until Season 7's "The Sl***y Pumpkin Returns" that she is given an identity. Ted discovers that the Sl***y Pumpkin is Naomi, a marine biologist played by none other than Joey Potter herself, Katie Holmes.

After her "Dawson's Creek" days, Holmes did not do much television in the 2000s. Her "HIMYM" role came after her turn as Jackie Kennedy in the Emmy-nominated miniseries "The Kennedys." It's too bad that Holmes only appeared here and in a brief flashback in Season 9's "The Poker Game." The Sl***y Pumpkin and Hanging Chad weren't meant to be.

The "Firework" singer played a key role in Season 6 despite the gang failing to remember her name. In the episode "Oh Honey," Zoey sets Ted up with her gullible cousin. Since Future Ted (Bob Saget) forgets her name in recounting the story, he simply refers to her as "Honey." Even though Ted and Honey start to hit it off, Barney is the one more interested in Honey, and Ted realizes he's in love with Zoey. The only problem? Zoey is married to The Captain (Kyle MacLachlan).

Honey's importance doesn't stop there. When Honey and Barney do go off together, Barney actually breaks down after she accidentally reminds him of his absent father who he recently reached out to. She's also the one to tell Marshall that Zoey is divorcing The Captain, meaning Zoey and Ted can actually be together. Honey helps Zoey not be "the one that got away" for Ted.

Dale Cooper trades "Twin Peaks" for the Big Apple as George Van Smoot, mostly called The Captain. He originally is introduced as Zoey's husband in Season 6 at a gala in "Natural History." Even after Zoey and The Captain split up, he still remains in the picture long after Ted and Zoey's relationship comes and goes. In Season 8, he hires Lily as his art consultant after she demonstrates a keen eye for art.

However, the Captain's lore with "HIMYM" goes even deeper thanks to a deleted scene from Season 9. Way back in Season 1, Ted wakes up in bed with a pineapple by his bed after a late night out and no recollection how it got there in an episode called "The Pineapple Incident." A deleted scene released to BuzzFeed reveals that George observes a maritime tradition of leaving a pineapple outside his front porch. Pineapples have a rich history of meaning, but in The Captain's case, the pineapple he left outside is a symbol of hospitality. Ted pieces together that this is where he got the pineapple all those years ago, thus solving this unsolved mystery.

Before Lin-Manuel Miranda became a household name thanks to "Hamilton," the songwriter is simply a passenger on the bus to Farhampton in Season 9's "Bedtime Stories." Marshall is on his way to Barney and Robin's wedding weekend and attempts to get his newborn son to sleep through rhyming stories. Miranda's character, Gus, lends his rapping skills to keep the rhyming going.

At this point in his career, Miranda had already released his Tony-winning musical "In the Heights" but wasn't as well-known. Prior to this, he had done a handful of spots on "House," "Modern Family," and even "The Sopranos." It turns out Miranda went to the same college as "HIMYM" creators Carter Bays and Craig Thomas, and in the years since their collegiate days, the three became friends. It would be two years later that "Hamilton" would debut on Broadway, and the rest, as they say, is history.

Three years before Lucy Hale became a pretty little liar, she was Robin's younger sister Katie. In Season 2's "First Time in New York," Katie comes to town to visit her big sister, but she's not alone. Katie brings her boyfriend, Kyle (Ryan Pinkston), with her, and she plans to lose her virginity to him. Robin spends much of Katie's visit trying to convince her little sister to wait until she's in love. When Katie decides to wait, Kyle dumps her. Before she leaves, the gang takes Katie to the Empire State Building.

In the final season, Katie returns for Barney and Robin's big wedding weekend as part of the bridal party. The sisters play hockey, watch movies, and bring a chill vibe to Robin's wedding day. Even with just two appearances, Hale and Smulders kept that Scherbatsky sisterhood strong.

In Season 4's "The Best Burger in New York," Marshall is on the hunt to find the best burger in New York, which also happens to be his first burger in the city. It's a perfect burger that's haunted not only him but the "Who Wants to Be a Millionaire?" host Regis Philbin. When Marshall initially searches for this burger spot, Barney connects Marshall with Philbin at his gym. Marshall makes a promise to contact Philbin if he ever finds it. 

As the gang makes another search for Marshall's specific burger spot, they update Philbin as they go. Although they initially lead him to the wrong spot, the episode culminates with Marshall and Philbin reuniting with their beloved burger; though it does take Philbin a second to be convinced it's the right burger. Marshall's passion and intensity to find his beloved burger is well-matched by the "Live!" host, making him a memorable "HIMYM" guest star.

Robin Sparkles made a name for herself as a Canadian teen pop star with her first hit "Let's Go to the Mall." For the follow-up, her second single was the love ballad "Sandcastles in the Sand." In Season 3's episode of the same name, Robin reunites with an ex-boyfriend played by "Dawson's Creek" star James Van Der Beek. The two briefly date and break-up again. When Barney comforts her after the break-up, Robin shows him the "Sandcastles in the Sand" music video. It features both Van Der Beek and Alan Thicke. However, the biggest and most surprising cameo of them all was the '80s teen pop star Tiffany.

In Season 3, Robin Sparkles' story mirrored other '80s one-hit wonder teen stars like Debbie Gibson and Tiffany, who was most known for her big hit single "I Think We're Alone Now." In Season 8, the introduction of Robin Daggers evolved her music career on an Alanis Morissette path. Still, Tiffany's cameo here was a great nod to that era of music.