Yahoo wants TV ad dollars, whether they be spent on original programming or augmenting TV spots.

During its Digital Content NewFronts presentation on Monday night, Yahoo presented its plans to siphon some of the $68 billion advertisers are expected to spend on U.S. TV this year. Those plans include: TV-length shows, live programming and the ability to retarget TV viewers with ads on Yahoo sites.

Next year Yahoo will premiere two half-hour comedies that will mark the portal's first foray into TV-style long form programming. "Other Space" will be an outer-space laffer created by "Bridesmaids" director-and-producer Paul Feig. And "Varsity Blues" producer Mike Tollin and "The Office" director Bryan Gordon have teamed on "Sin City Saints," a work-comedy set in a fictional pro basketball team's front office. Both shows will release all eight of their episodes at once, a la Netflix with "House of Cards."

Yahoo plans to announce at least two more long form shows in the next two months, according to a Yahoo spokesperson.

Yahoo is also producing two new shows with global news anchor Katie Couric. In addition to the interview series she has been filming for Yahoo News, "World 3.0" will highlight people "who are 'hacking' life as we know it," according to a company announcement. Ms. Couric's other new show, "Now I Get It," looks to be the video version of the company's news-summary app Yahoo News Digest. Each of the program's short videos will explain the day's news and be designed for social sharing.

Live programming
In addition to scheduling scripted and non-scripted series, Yahoo is also ordering up some live programming. The company has partnered with live-events giant Live Nation to create a dedicated video channel on the Yahoo Screen streaming service. The channel will air music performances and artist interviews, and the two companies will co-produce a year's worth of daily concert livestreams. Kellogg's has signed on the sponsor the channel.

A major consideration for media buyers will be whether Yahoo's new shows can deliver enough eyeballs to merit their ad dollars. The six shows Yahoo presented at last year's NewFronts have combined to receive a paltry 13 million views. Of those series, "Tiny Commando" was the only show to secure a sponsor (Energizer), while a number of advertisers bought ads against Yahoo's three-show comedy slate. The three lifestyle shows Yahoo presented did not receive sponsors.

TV-like measurement
To assuage advertisers used to the way their TV ads are measured, Yahoo has partnered with comScore to validate campaigns' demographic targets. The hope is the measurement will create a more apples-to-apples comparison with TV and make buyers more comfortable bringing their budgets online.

Yahoo isn't only selling its own content. Borrowing Twitter's and Facebook's strategy as a TV advertiser's best friend, the company is also pitching advertisers on a new way to augment their TV buys. The company will be using its recently updated Smart TV service and registered user base to retarget people who see a brand's spot on traditional TV with ads online. Yahoo Americas chief Ned Brody said the company has been able to "link back on an 80% basis to our cookie pools." However the program has its own size issues. Yahoo's Smart TV software currently runs on just over 2 million TVs, though Mr. Brody said that number will hit 4 million by the end of the year.

Taking advantage of all the brand marketers tuned in to NewFronts, Yahoo also announced a new so-called "digital magazine," Yahoo Travel. As with predecessors Yahoo Tech and Yahoo Food, the new lifestyle property will run sponsored articles and videos. Las Vegas and Walt Disney Parks and Resorts have signed on as launch sponsors.