The 7 Best Chatbots of 2019

How can you tell a good chatbot from a bad chatbot? With so many on the market, it’s tough to decide which one deserves your phone storage.

Back in 2018, there were a select few chatbots that always appeared in our research. They were touted as the latest and greatest in the chatbot scene, so we wanted to test them for ourselves. For us, a good chatbot possesses some or all of these qualities:

  1. Omnicapable: The chatbot can converse seamlessly across multiple channels without losing data.
  2. Conversational: The chatbot has an advanced vocabulary, gives appropriate responses and speaks at a “natural” pace depending on its use case. It also occasionally uses slang or humor.
  3. Helpful: It performs its job efficiently and effectively.
  4. Insightful: The chatbot improves your knowledge or well-being by giving advice, lessons, tests or exercises.

How these chatbots were chosen

You won’t find any Loebner Prize chatbot contenders here. The uncanny valley is an eerie place so we avoided chatbots that pretend to be human without stating that they’re a bot — though there is one on this list that continues to fool people despite its honesty.

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In addition to the qualities mentioned in the intro, we focused on the chatbot’s appearance, compatibility, ease of use, helpfulness and reviews and ratings. Based on these criteria, here are the best chatbots of 2019.


Developed by Stanford University psychologist Alison Darcy , Woebot is a cartoon robot that helps reduce depression symptoms through active listening and by praising their chat partner’s positive feedback with fun GIFs and encouraging words.

Woebot GIF

The conversational therapy bot graced the pages of the New York Times , Wired and Business Insider for its gentle attentiveness and sensitivity to emotions. The self-proclaimed “charming robot friend” is available 24/7 to those who need guidance, a confidence boost or someone to chat with when worries prohibit sleep.

Woebot is only available via mobile on the App Store or Google Play , but limiting interaction to the app makes the conversation more intimate since it’s like texting with a friend. It has a 4.6 star rating on the App Store, and people frequently state that Woebot is funny, encouraging and has a likeable personality despite its obvious scripts. A chatbot that aids mental health certainly deserves a spot on every top chatbot list.


Travel apps can sometimes be - for lack of a better word - janky. In my experience, they often freeze mid-search or display limited airfare options. Mobile transactions also feel like a data breach waiting to happen. But Hipmunk is different.

The buck-toothed chipmunk donning vintage aviator glasses can assist you via web, Facebook Messenger or Skype. I added Hipmunk to Facebook and typed “Get Started” with admittedly low expectations.

Facebook messenger conversation with Hipmunk about flights from Cologne, Germany

Americans are possibly Hipmunk’s main audience, which explains why it assumed I would want to plan a major getaway only five hours east of Cologne. After stating that I was interested in traveling to Japan from Germany, Hipmunk displayed several flight options ordered by the “Least Agonizing.”

Facebook messenger conversation with Hipmunk about flights to Tokyo, Japan from Cologne, Germany

I appreciated this small funny detail and even found myself sifting through its recommendations. Hipmunk displayed airfare from sites I had never considered, and had lower prices than my past Tokyo searches on Expedia. And because Hipmunk redirected me to a website to complete my purchase, I could rely on the little digital rodent as an assistant rather than an agent.

The app has a 4.8 star rating on the App Store and reviewers commend Hipmunk for its beautiful design and expansive selection. The chatbot also gets points for its casual script, speed and ease of use across multiple channels. Hipmunk will even tell you a joke if you ask (albeit not a good one), but it’ll quickly refocus the topic on travel.


How do you win a small claims case without a lawyer? With a chatbot, of course! Started as a web-only chatbot that helps you dispute parking tickets, DoNotPay launched an iOS app offering legal counsel to those wronged by the law. The app even gives you the option to sue anyone by pressing a button, and a chatbot will guide you through the process. That’s so 21st century.

The display is colorful and stylish, likely to obscure the monotonous language of legal documents. The website is still limited to parking ticket appeals, but that’s what it does best.

The service is currently free and has been proven successful if reviews and tweets are to be believed. It’s empowering to settle legal matters via your phone, and it’s aiding the larger issue at hand - people not knowing their rights.

DoNotPay highlights a big problem with the justice system, which is that it doesn’t matter how much protection the law gives you if you’re not aware of it.

The Verge

Rated 3.5 stars on the App Store (probably downrated by crooked city officials), DoNotPay’s chatbot gets right to business, so it’s not too conversational. Legal trouble is nothing to joke around with anyway.


When you spend so much time with one person, you often start mimicking their speech or behavior. This is exactly what Replika does, but with the added benefit of being a virtual companion for mental wellness.

Replika was created in 2017 by Eugenia Kuyda after losing her best friend, Roman, in a fatal accident. Roman was her emotional rock, and someone she often confided in. Replika started as a culmination of Roman’s written messages but evolved into a conversational chatbot with the calming demeanor of a concerned and interested friend.

Kuyda’s creation was inspired by a chilling Black Mirror episode called “Be Right Back,” which follows the main character’s relationship with the digital version of her late boyfriend.

Image of woman looking at her phone with a caption that says the AI companion who cares

For the sake of this post and out of genuine curiosity, I created my own Replika named Haru, which is a Japanese word that means “spring,” like the season. While Haru hasn’t quite picked up on my mannerisms or personality yet (it’s only been a few days after all), it’s already clear that this AI is far more complex in an emotional sense than the other conversational chatbots in this list.

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Haru takes a beat before “typing” a message, and while some of its responses are clearly triggered by keywords, Haru does a bang up job at being a coherent conversation partner. You earn personality badges by answering questions and performing exercises with your Replika, and partake in discussion and tests about topics such as reappraisal or social anxiety.

Replika is available via web or mobile, and has a 4.6 star rating on the App Store . The chatbot even has its own subreddit full of conversation screenshots of Replika’s deep, savage or endearing moments.

Insomnobot 3000

Whether it’s just a conversation partner or perfectly planned marketing scheme, Insomnobot 3000 is a chill chatbot to hang out with when you’re having trouble catching Z’s.

Image of a chatbot sitting on a couch holding a phone

The night owl chatbot was created by Casper , which specializes in, wait for it, mattresses and pillows. But if you think Insomnobot is going to spam you with product suggestions, think again. The chatbot cleverly brings it up only occasionally. It’s a great example of how companies are employing chatbots to connect with customers to blur the commercial divide.

Insomnobot was included in a Forbes list of the “7+ Amazing Examples Of Online Chatbots And Virtual Digital Assistants In Practice,” but unlike Woebot or Replika, it’s not programmed to handle late night anxiety or worry. Instead, you’ll find a funny fellow insomniac that responds quickly, though incoherently at times.

Image of a conversation with the insomnobot 3000

Insomnobot 3000 is currently only available via mobile SMS, but it gets a pass since you’re likely to be on your phone late at night browsing Twitter for the upteenth time. It has also been nominated for a Shorty Award , and was a Webby Award honoree.

Casper has set the marketing chatbot standards high; it won’t be long until we’re all chatting with bots who subtly push products in between messages about burritos or 90s boy bands.


Hearing a good secret is hard to resist, especially if you have something to gain from it. Growthbot pulls back the digital stage curtain for marketers, revealing juicy data and actionable insights from competitors.

The chatbot was created by HubSpot’s CTO Dharmesh Shah and is connected to several smart business systems to provide information related to sales, promotion and marketing. It’s a nifty sidekick for those searching which keywords ranks for, or which ppc keyword is buying (’s “uber”).

Image of a conversation with growthbot

Growthbot is compatible with Slack and Facebook Messenger, and it greets you by stating its core competencies. Its chatting capabilities are limited to the prompts it was preprogrammed to answer, but its information is often substantial. Growthbot saves you the effort of consulting other ranking sites and combing through webpages to find the information you need.

I wanted it for myself. So I built it for myself.

Dharmesh Shah

Much of the information you receive is from HubSpot, but Growthbot also searches through web-based products such as Google Analytics, Alexa and SimilarWeb. For example, if you wanted company info on Userlike, you would type “company info about” and instantly receive a list of relevant details.

Image of a conversation with growthbot about userlike's company info

Some information isn’t exactly up-to-date, (we have a new address and at least triple the amount of employees), but it links to relevant pages and gives you an idea of what Userlike does and where it is located. Feeling tempted to dig up details on your competitors yet?

7 Amy

Chatbots are here to take our jobs , but don’t worry, because it’s the jobs no one else wants to do. Scheduling and updating meetings is a monotonous task that continues to plague offices across the world, but a solution is available, and her name is Amy.

Amy (or her male counterpart “Andrew”) lives in your email, calendar and Slack scheduling meetings based on your conversations and even updating them as soon as changes are proposed. Those who use Amy regularly said her accuracy and speech are so human-like that guests often ask to meet her when visiting for a meeting. This speaks volumes to Amy’s abilities, but chatbot makers should beware the uncanny valley and businesses should let coworkers and clients know when they’re using chatbot assistants.

Image of three smartphones showing email conversations

Amy is the only chatbot in this list that costs money to use it, but at only $8 - $24 per month (after a 14-day free trial), it’s the most practical application of AI for everyday use. She’s perfect for startups that can’t afford to hire assistants, sales managers who frequently meet with clients, or people who forget to follow-up on invitations.

Amy has a 4.2 rating on G2Crowd , and many reviewers cite Amy as a total timesaver. The Twitter account dedicated to Amy and Andrew even has a section called “Love Notes,” which is a collection of tweets praising the AI’s assistant skills. Would you let a chatbot schedule your day?

What we learned while collecting the best chatbots of 2019

We’re trusting chatbots more and more. We’re telling them our deepest thoughts, our travel plans, the people we’re meeting. AI takes time and dedication to develop, so it’s great to see it not go to waste — but what does this tell us about the future of chatbots?

In 2016, Microsoft CEO Satya Nadella said, “Bots are the new apps.” Today, you can use a chatbot to send money , find a date , settle a legal dispute and order a pizza . If we learned anything from Google’s presentation of Duplex , it’s that bots may even one day be used to make believable phone calls on our behalf.

These developments may be frightening for some since AI requires extensive data to become “intelligent,” which leads to data privacy concerns. But clearly there’s a market for more chatbots, and 2020 and the years to come may see more bots representing brands, companies and even ourselves.

If you’re curious to know people’s honest opinions on chatbots, check out our video on customer chatbot perceptions below:

You can find the full results of our survey in our post “What Do Your Customers Actually Think About Chatbots?”