from Heartbreakers (2001)

  • Heartbreakers

    Jennifer Love Hewitt

    Jennifer Love Hewitt wearing a low-cut short grey dress that she uses to show off her legs and butt as she bends over in a guy's office. She then approaches his desk and leans over, giving him a great view of her cleavage in close-up. She then pretends to drop the papers and bends over on the floor, kneeling as the guy then kisses her. She jumps into his arms with her legs wrapped around him, her butt in her panties in view. The guy carries her over to his desk and sits so that she can begin to go down on him. From Heartbreakers.

    Sexy 2:02 - 42.51 MB - 1280x548 px July 10th, 2015 @ 2:36 pm Jennifer Love Hewitt - Heartbreakers - 1.mp4

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  • Heartbreakers

    Jennifer Love Hewitt

    Jennifer Love Hewitt in a skimpy pink dress, baring some bouncing cleavage as she walks up to a valet at a car park and distracts him so she can sneak a set of keys and break into a car. From Heartbreakers.

    Sexy 1:30 - 31.32 MB - 1280x548 px July 10th, 2015 @ 2:34 pm Jennifer Love Hewitt - Heartbreakers - 2.mp4

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  • Heartbreakers

    Jennifer Love Hewitt

    Jennifer Love Hewitt showing bouncing breasts and lots of cleavage as she walks into a bar wearing a very short tight pink dress with her bra exposed. She sits down on a table with her cleavage on display as she talks to a guy. She then looks over at a guy, sucking olives seductively off a toothpick before choking on one. Lastly, she shows more of her bra while leaning over and talking on a phone. From Heartbreakers.

    Sexy 3:49 - 79.57 MB - 1280x548 px July 10th, 2015 @ 2:32 pm Jennifer Love Hewitt - Heartbreakers - 3.mp4

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  • Heartbreakers

    Jennifer Love Hewitt

    Jennifer Love Hewitt showing cleavage in a revealing short pink dress as she squats by a road and rolls out some tire spikes to cause a car accident. She then walks over to the crashed car and talks to a guy for a while before she pushes him out of view when another car approaches and she rolls down a hill after him, flashing her panties. From Heartbreakers.

    Sexy 1:38 - 33.88 MB - 1280x548 px July 12th, 2015 @ 6:26 pm Jennifer Love Hewitt - Heartbreakers - 4.mp4

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  • Heartbreakers

    Jennifer Love Hewitt

    Jennifer Love Hewitt wearing a low-cut blue tank top that shows nice cleavage along with her tight white jeans as she walks into a hotel room and talks to Sigourney Weaver, who is wearing a robe that shows a bit of her bra underneath. From Heartbreakers.

    Sexy 1:06 - 22.83 MB - 1280x548 px July 12th, 2015 @ 6:24 pm Jennifer Love Hewitt - Heartbreakers - 5.mp4

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  • Heartbreakers

    Jennifer Love Hewitt

    Jennifer Love Hewitt jogging up a stairway, causing her cleavage to bounce a bit in her skimpy blue tank top. A guy then opens the door for her and she makes out with him, pulling her tank top off and showing her bra from the side as she lays down on top of him on a sofa in her tight white jeans and blue bra. From Heartbreakers.

    Sexy 1:23 - 28.70 MB - 1280x548 px July 12th, 2015 @ 6:21 pm Jennifer Love Hewitt - Heartbreakers - 6.mp4

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  • Heartbreakers

    Jennifer Love Hewitt

    A very nice close-up view of Jennifer Love Hewitt's magnificent cleavage as she bends over to talk to Ray Liotta at his desk. Hi-res DVD capture from Heartbreakers.

    Sexy 0:39 - 9.31 MB - 720x304 px November 29th, 2001 @ 7:22 pm [email protected]

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  • Heartbreakers

    Jennifer Love Hewitt

    Jennifer Love Hewitt bending down to pick up some papers and having her dress ride up to expose her panties as she jumps into Ray Liotta's arms and kisses him. Hi-res DVD capture from Heartbreakers.

    Sexy 0:53 - 12.76 MB - 720x304 px November 29th, 2001 @ 7:20 pm [email protected]

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  • Heartbreakers

    Jennifer Love Hewitt

    More of Jennifer Love Hewitt's bouncing cleavage as she walks up to a valet and distracts him in order to steal a set of keys. Hi-res DVD capture from Heartbreakers.

    Sexy 0:48 - 11.52 MB - 720x304 px November 29th, 2001 @ 7:19 pm [email protected]

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  • Heartbreakers

    Jennifer Love Hewitt

    Jennifer Love Hewitt having her awesome breasts bounce nicely as she walks into a bar wearing a very tight short pink dress that shows a lot of cleavage. Hi-res DVD capture from Heartbreakers.

    Sexy 0:33 - 7.79 MB - 720x304 px November 29th, 2001 @ 7:18 pm [email protected]

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  • Heartbreakers

    Jennifer Love Hewitt

    Jennifer Love Hewitt showing some great cleavage as she sits at a table in a short pink dress, then gets up to use the cigarette machine. Hi-res DVD capture from Heartbreakers.

    Sexy 0:49 - 11.40 MB - 720x304 px November 29th, 2001 @ 7:17 pm [email protected]

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  • Heartbreakers

    Jennifer Love Hewitt

    Jennifer Love Hewitt seductively sucking some olives off a toothpick and then choking on one, all while wearing a great tight pink dress. Hi-res DVD capture from Heartbreakers.

    Sexy 0:48 - 11.21 MB - 720x304 px November 29th, 2001 @ 7:16 pm [email protected]

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  • Heartbreakers

    Jennifer Love Hewitt

    A nice quick clip of Jennifer Love Hewitt showing her bra from underneath her pink dress as she leans over. Hi-res DVD capture from Heartbreakers.

    Sexy 0:09 - 2.00 MB - 720x304 px November 29th, 2001 @ 7:15 pm [email protected]

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  • Heartbreakers

    Jennifer Love Hewitt

    More of Jennifer Love Hewitt and her cleavage in her great pink dress as she argues with Jason Lee on a road. Hi-res DVD capture from Heartbreakers.

    Sexy 0:47 - 10.89 MB - 720x304 px November 29th, 2001 @ 7:14 pm [email protected]

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  • Heartbreakers

    Jennifer Love Hewitt

    Jennifer Love Hewitt showing some cleavage in a tight blue top and very tight white jeans. Hi-res DVD capture from Heartbreakers.

    Sexy 0:59 - 14.21 MB - 720x304 px November 29th, 2001 @ 7:12 pm [email protected]

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  • Heartbreakers

    Jennifer Love Hewitt

    Jennifer Love Hewitt removing her top to expose a blue bra as she jumps on the couch with Jason Lee and they kiss. Hi-res DVD capture from Heartbreakers.

    Sexy 0:25 - 5.82 MB - 720x304 px November 29th, 2001 @ 7:09 pm [email protected]

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  • Heartbreakers

    Jennifer Love Hewitt

    Jennifer Love Hewitt showing lots of jiggling cleavage as she runs on a treadmill wearing a sports bra in this deleted scene. Hi-res DVD capture from Heartbreakers.

    Sexy 0:34 - 7.30 MB - 624x272 px January 17th, 2002 @ 11:01 pm [email protected]

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from Confessions of a Sociopathic Social Climber (2005)
 
from The Client List (2011)
 
from The Truth About Love (2005)

  • The Truth About Love

    Jennifer Love Hewitt

    Jennifer Love Hewitt taking her shirt off to reveal a beige bra and then walking across a room and climbing into bed with a guy and kissing him before falling asleep. Hi-res DVD capture from The Truth About Love.

    Sexy 0:21 - 5.89 MB - 720x400 px May 3rd, 2006 @ 7:17 pm [email protected]

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  • The Truth About Love

    Jennifer Love Hewitt

    Jennifer Love Hewitt wearing some low cut white lingerie that shows some nice cleavage as she waits for a guy to notice her and then sitting down on a bed next to him and kissing him briefly before talking to him for a bit. Hi-res DVD capture from The Truth About Love.

    Sexy 0:46 - 10.96 MB - 720x400 px May 7th, 2006 @ 7:56 pm [email protected]

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  • The Truth About Love

    Jennifer Love Hewitt

    Jennifer Love Hewitt wearing a red bustier that shows some nice cleavage as she works out and then tries smoking and drinking before being seen in the reflection of a mirror on the ground as the camera pans up to reveal her in thigh-high stockings with a red robe around her shoulders. Hi-res DVD capture from The Truth About Love.

    Sexy 0:32 - 7.73 MB - 720x400 px May 3rd, 2006 @ 7:15 pm [email protected]

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  • The Truth About Love

    Jennifer Love Hewitt

    Jennifer Love Hewitt opening her trenchcoat to reveal a lot of cleavage in a red bustier as she yells at a guy until he walks over to her. Hi-res DVD capture from The Truth About Love.

    Sexy 0:14 - 3.43 MB - 720x400 px May 7th, 2006 @ 7:54 pm [email protected]

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  • The Truth About Love

    Jennifer Love Hewitt

    Jennifer Love Hewitt sucking a guy's finger to remove a ring from it and then taking off her robe to reveal some red lingerie before having sex with him in a very tame love scene. Hi-res DVD capture from The Truth About Love.

    Sexy 1:18 - 18.68 MB - 720x400 px May 9th, 2006 @ 6:57 pm [email protected]

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  • The Truth About Love

    Jennifer Love Hewitt

    Jennifer Love Hewitt wearing a red tanktop and black tutu devil style outfit as she poses for Kate Miles and then sticking her butt out in black panties and fishnet stockings from behind a curtain before jumping on a couch and letting Kate slap her on the ass. Hi-res DVD capture from The Truth About Love.

    Sexy 0:10 - 2.49 MB - 720x400 px May 1st, 2006 @ 6:42 pm [email protected]

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  • The Truth About Love

    Jennifer Love Hewitt

    Jennifer Love Hewitt spinning in slow motion causing her dress to lift up and giving us a look at her thigh-high stockings and ass in white panties. Hi-res DVD capture from The Truth About Love.

    Sexy 0:05 - 1.06 MB - 720x400 px May 1st, 2006 @ 6:40 pm [email protected]

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  • The Truth About Love

    Jennifer Love Hewitt

    Jennifer Love Hewitt adjusting herself on a massage table in slow motion and giving us a nice look at her cleavage and her back as Kate Miles watches while topless and lying on her stomach with her breasts pressed against the table. Hi-res DVD capture from The Truth About Love.

    Sexy 0:22 - 4.90 MB - 720x400 px May 5th, 2006 @ 6:00 pm [email protected]

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  • The Truth About Love

    Jennifer Love Hewitt

    Jennifer Love Hewitt lying topless on a massage table with her breasts pressed against it as she talks with Kate Miles before Kate gets up and walks over and sits down next to her to talk some more. Hi-res DVD capture from The Truth About Love.

    Sexy 0:54 - 13.02 MB - 720x400 px May 9th, 2006 @ 6:56 pm [email protected]

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from Ghost Whisperer (2005)
 
from If Only (2004)

  • If Only

    Jennifer Love Hewitt

    Jennifer Love Hewitt wearing a pink and black nightgown with a see-through black lace top and black stars covering her nipples as she lies in bed making out with a guy and talking with him before she jumps up out of bed giving us some more looks at the sides of her breasts while she talks with the guy some more and makes her way across the room. From If Only. Updated to higher quality.

    Sexy 0:31 - 37.41 MB - 1920x1080 px July 4th, 2022 @ 2:22 pm Jennifer Love Hewitt - If Only - 1.mp4

  • If Only

    Jennifer Love Hewitt

    Jennifer Love Hewitt seen in silhouette changing behind a screen and then walking out and surprising a guy by opening a jacket to reveal her body in a white lace bra and panties as she lets him check her out for a bit before he picks her up and carries her over to a bed making out with her and then has her sit up giving us a better look at her cleavage. Next, we see her follow him into a bathroom where she jumps up on a sink and wraps her legs around him and then has him carry her over to a shower. Finally, she goes back into the bedroom and lies down on the bed giving us another look at her cleavage. From If Only. Updated to higher quality.

    Sexy 1:41 - 124.79 MB - 1920x1080 px July 4th, 2022 @ 2:25 pm Jennifer Love Hewitt - If Only - 2.mp4

  • If Only

    Jennifer Love Hewitt

    Jennifer Love Hewitt wearing a very slightly see-through white crop top and white panties that show a hint of her nipples and her ass in a pair of darker black thong panties underneath as she tries to calm a guy down who is panicking and then goes behind a screen and changes while leaning out and holding her breasts before she emerges wearing only a jacket and then surprises him by dropping the jacket to flash him giving us a look at her bare back. From If Only. Updated to higher quality.

    Sexy 1:24 - 104.55 MB - 1920x1080 px July 4th, 2022 @ 2:28 pm Jennifer Love Hewitt - If Only - 3.mp4

  • If Only

    Jennifer Love Hewitt

    Jennifer Love Hewitt slowly and passionately kissing a guy in front of a fire place and then removing her shirt showing her cleavage in a strapless bra as she goes back to kissing him while she pulls him on top of her onto the ground and then rolls over on top of him showing the bra and her ass in tight jeans before he unclasps her bra and lets it hang down showing the side of her right breast from the top and bottom all as they continue to make out. From If Only. Updated to higher quality.

    Sexy 0:50 - 54.14 MB - 1920x1080 px July 4th, 2022 @ 2:31 pm Jennifer Love Hewitt - If Only - 4.mp4

  • If Only

    Jennifer Love Hewitt

    Jennifer Love Hewitt wearing an white top with a see-through lace front as she rushes down the sidewalk with a guy while trying to protect herself from the rain using a jacket before they get into the back of a taxi and then start making out while showing her hard nipples in the wet white top. From If Only. Updated to higher quality.

    Sexy 1:47 - 132.83 MB - 1920x1080 px July 4th, 2022 @ 2:20 pm Jennifer Love Hewitt - If Only - 5.mp4
 
from The Suburbans (1999)
 
from Party of Five (1994)
 
from Entertainment Tonight (1981)
 
from Tuxedo (2002)

  • Tuxedo

    Jennifer Love Hewitt

    Jennifer Love Hewitt showing some great cleavage in a collection of scenes, including one in which she is seen underwater in a pool, possibly showing some nipple. From Tuxedo.

    Sexy 0:39 - 9.34 MB - 320x240 px May 2nd, 2003 @ 7:50 pm JLH-Tuxedo-beercaps.mpeg
 
from MTV's Making the Video: Barenaked
 
from I Still Know What You Did Last Summer (1998)
 
from The Client List (2010)
 
from Time of your Life (1999)
 
from Trojan War (1997)
 
from Boy Meets World (1993)

  • Boy Meets World

    Jennifer Love Hewitt

    Jennifer Love Hewitt wearing a tight top that shows off her breasts as she talks with a guy in a high school hallway before he pushes her up against the lockers and starts passionately making out with her and kissing her neck before they get interrupted by Danielle Fishel, Trina McGee and some guys when suddenly a phone rings and Jennifer jumps and screams causing her breasts to bounce and jiggle around. The bouncing portion then repeats in slow motion giving us a better look at the jiggling. From Boy Meets World. Updated to higher quality.

    Sexy 1:03 - 14.07 MB - 640x480 px July 1st, 2019 @ 6:14 pm Jennifer Love Hewitt - Boy Meets World - S04E17.mp4

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from I Know What You Did Last Summer (1997)
 
from E! Grammy Preshow
 
from E!
 
from The Tonight Show with Jay Leno (1992)
 
from Grammys

  • Grammys

    Jennifer Love Hewitt

    Jennifer Love Hewitt wearing a strapless red dress with her breasts pushed up showing off a lot of cleavage as seen in a quick clip while on the red carpet at the Grammys.

    Sexy 0:03 - 0.54 MB - 352x240 px November 19th, 2005 @ 11:28 pm JLH - MTV Boobs.mpeg
 
from Extra (1994)
 
from Access Hollywood (1996)
 
from VH1 Fashion Awards
 
from The Ellen DeGeneres Show (2003)
 
from The Late Late Show with Craig Ferguson (2005)
 
from Late Night with Conan O'Brien (1993)
 
from Last Call with Carson Daly (2002)
 
from The Devil and Daniel Webster (2003)
 
from Various Sources

  • Various Sources

    Jennifer Love Hewitt

    An early clip of JLH doing a cheerleader routine.

    Sexy 0:49 - 6.28 MB - 320x240 px January 9th, 2000 @ 11:30 pm !JLH-Cheerleader.mpg

  • Various Sources

    Jennifer Love Hewitt

    JLH in a very tight pair of pink jeans and top from a stylish Japanese Levi's commercial.

    Sexy 0:30 - 5.00 MB - 352x240 px May 9th, 2000 @ 7:45 pm cm_-_jennifer_love_hewitt_-_levis_colors.mpg

  • Various Sources

    Jennifer Love Hewitt

    JLH in a very tight pair of blue jeans and top from a stylish Japanese Levi's commercial.

    Sexy 0:30 - 5.00 MB - 352x240 px May 9th, 2000 @ 7:46 pm cm_-_jennifer_love_hewitt_-_levis_cut_in.mpg

  • Various Sources

    Jennifer Love Hewitt

    Jennifer Love Hewitt wearing a halter top that shows off her nice cleavage as she hosts the 2002 World Music Awards.

    Sexy 0:25 - 6.10 MB - 352x240 px April 23rd, 2002 @ 2:44 pm down-Jennifer_Love_Hewitt-World_Music_Awards-2002-04-21-hb.mpg

  • Various Sources

    Jennifer Love Hewitt

    Jennifer Love Hewitt wearing a white tanktop with the words 'Love Boat' printed across her chest and showing off her sexy stomach as she poses for a photoshoot.

    Sexy 1:42 - 20.41 MB - 320x240 px February 17th, 2004 @ 2:41 pm [email protected]

  • Various Sources

    Jennifer Love Hewitt

    Jennifer Love Hewitt wearing a black halter top and dancing a bit for the camera while presenting at The Teen Choice Awards.

    Sexy 0:19 - 3.19 MB - 320x240 px January 25th, 2003 @ 7:47 pm jlh-hottie-quickjob.mpg

  • Various Sources

    Jennifer Love Hewitt

    A quick clip of a young Jennifer Love Hewitt walking down a runway in green shorts and a green bikini top while holding a basketball.

    Sexy 0:04 - 0.35 MB - 320x240 px May 17th, 2003 @ 11:26 pm jlh-runway.mpeg

  • Various Sources

    Jennifer Love Hewitt

    Jennifer Love Hewitt wearing a white tanktop and blue jeans while briefly performing at Wango Tango and then wearing a black top and jeans backstage and turning around giving us a look at her butt from VH1.

    Sexy 0:19 - 4.58 MB - 320x240 px August 29th, 2003 @ 8:48 pm JLH-WT2003-beercaps.mpg

  • Various Sources

    Jennifer Love Hewitt

    JLH wearing a lowcut dress that shows some nice cleavage as she closes the 2001 Teen Choice Awards.

    Sexy 0:09 - 2.30 MB - 320x240 px August 22nd, 2001 @ 5:52 pm JLH08212001-beercaps.mpg

  • Various Sources

    Jennifer Love Hewitt

    Jennifer Love Hewitt seen rolling over on the beach in a bikini in this nice slow-motion extract of another clip. She shows lots of cleavage - watch for a possible nipple slip. From a VH1 video countdown.

    Sexy 0:23 - 5.00 MB - 320x240 px November 21st, 2002 @ 4:31 pm JLH11152002-beercaps.mpg

  • Various Sources

    Jennifer Love Hewitt

    Jennifer Love Hewitt showing some lovely cleavage in a bikini in this collection of scenes while hosting a VH1 video countdown. Includes a great scene of her rolling over as her breasts almost pop out. Part 1 of 2.

    Sexy 2:24 - 34.84 MB - 320x240 px November 21st, 2002 @ 4:37 pm JLH11162002-beercaps_a.mpg

  • Various Sources

    Jennifer Love Hewitt

    Jennifer Love Hewitt in a collection of scenes while hosting a VH1 video countdown. We see her looking very sexy in a couple different bikinis while on the beach. Part 2 of 2.

    Sexy 2:14 - 32.44 MB - 320x240 px November 21st, 2002 @ 4:35 pm JLH11162002-beercaps_b.mpg